RSC - Org. Biomol. Chem. latest articles

Microwave-Assisted C-3 Selective Oxidative Radical Alkylation of Flavones.

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25249J, Communication

Luis D. Miranda, Marco V. Mijangos, Joaquin Gonzalez-Marrero, Paulette Vincent-Ruz, Armando Lujan-Montelongo, Diana Olivera-Diaz, Elihu Bautista, Alfredo Ortega, Magdalena de la Luz Campos-Gonzalez, Rocio Gamez-Montano
Flavones were directly alkylated at the C-3 position in moderate yields using a xanthate-based oxidative radical addition procedure. This methodology is a suitable synthetic tool for the direct substitution of...
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Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07034K, Paper

Edward J. Emmett, Charlotte S. Richards-Taylor, Bao Ngoc Nguyen, Alfonso Garcia-Rubia, Barry R Hayter, Michael Willis
By using DABCO[middle dot](SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides...
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Synthesis of donor-acceptor chromophores by the [2 + 2] cycloaddition of arylethynyl-2H-cyclohepta[b]furan-2-ones with 7,7,8,8-tetracyanoquinodimethane

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06931H, Paper

Taku Shoji, Junya Higashi, Shunji Ito, Tetsuo Okujima, Masafumi Yasunami, Noboru Morita
A series of 2H-cyclohepta[b]furan-2-one-substituted dicyanoquinodimethanes (DCNQs) were synthesized by the formal [2 + 2] cycloaddition-cycloreversion sequence of the corresponding acetylene derivatives with TCNQ.
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Alteration of selectivity in rhodamine based probes for Fe(III) and Hg(II) ion induced dual mode signalling responses

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07182G, Communication

Bamaprasad Bag
The probes for metal ion induced chromo- and fluorogenic signalling responses alter their selectivity depending upon the nature of substituent as well as a function of solvent medium. 2 has...
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Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07122C, Communication

B. Ramachary Dhevalapally, Madhavachary R., Shiva Prasad M.
A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring group induced sequential Michael-lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the...
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Construction of highly functional [small alpha]-amino nitriles via a novel multicomponent tandem organocatalytic reaction: a facile access to [small alpha]-methylene [gamma]-lactams

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07112F, Communication

Feng Pan, Jian-Ming Chen, Zhe Zhuang, Yin-Zhi Fang, Sean Xiao-An Zhang, Wei-Wei Liao
The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized [small alpha]-amino nitriles, which could be readily converted into [small alpha]-methylene-[gamma]-butyrolactams.
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Mechanism and optimisation of the homoboroproline bifunctional catalytic asymmetric aldol reaction: Lewis acid tuning through in situ esterification

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06872A, Paper

Irene Georgiou, Andrew Whiting
The novel enamine-Lewis acid based chiral catalyst homoboroproline undergoes in situ esterification of the boronic acid to provide a highly effective asymmetric aldol catalyst.
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Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06841A, Paper

George E. Salnikov, Alexander M. Genaev, Vladimir G. Vasiliev, Vyacheslav G. Shubin
Interaction of the two simple compounds, CH₃CN and TfOH, results in formation of a variety of complicated structures, the composition of the reaction products being a function of the ratio of CH₃CN to TfOH.
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A Simple Synthesis of N-Perfluoroacylated and N-Acylated Glycals of Neuraminic Acid with a Cyclic Aminic Substituent at 4[small alpha] Position as Possible Inhibitors of Sialidases.

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07015D, Paper

Paola Rota, Pietro Allevi, Irene Sofia Agnolin, Roberto Mattina, Nadia Papini, Mario Anastasia
A simple protocol for the synthesis of N-perfluoroacylated and N-acylated glycals of neuraminic acid, having a secondary cyclic amines (morpholine or piperidine) at the 4[small alpha] position, has been set-up, starting...
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Kinetics studies of rapid strain-promoted [3+2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07165G, Paper

Craig S McKay, Mariya Chigrinova, Jessie Blake, John Paul Pezacki
Strain-promoted cycloadditions of cyclic nitrones with biaryl-aza-cycloooctynone (BARAC) proceed with rate constants up to 47.3 M-1s-1, this corresponds to a 47-fold rate enhancement relative to reaction of BARAC with benzyl...
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Reverse thioether ligation route to multimeric peptide antigens

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06819B, Paper

Marta Monso, Wioleta Kowalczyk, David Andreu, Beatriz G. De la Torre
Multimeric presentation, a rather effective way of enhancing peptide immunogenicity, is best exemplified by MAP (multiple antigenic peptide) dendrimers consisting of a branched Lys core on which several copies of...
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Fluorimetric detection of Mg2+ and DNA with 9-(alkoxyphenyl)benzo[b]quinolizinium derivatives

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06948B, Paper

Maoqun Tian, Heiko Ihmels, Shite Ye
A benzo[b]quinolizinium-benzo-15-crown-5 ether conjugate 2a is presented that enables the fluorimetric detection of Mg2+ and DNA by a significant light up effect, along with a change of the emission wavelength...
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Substituted Oxines Inhibit Endothelial Cell Proliferation And Angiogenesis

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06978D, Paper

Shridhar Bhat, Joong Sup Shim, Feiran Zhang, Curtis Chong, Jun Liu
Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated...
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Expedient synthesis of pseudo-Pro-containing peptides: towards constrained peptidomimetics and foldamers

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07172J, Paper

Rossella De Marco, Alessandra Tolomelli, Marilena Campitiello, Pasqualina Rubini, Luca Gentilucci
The reaction of sulfonyl peptides containing L- or D-configured Ser or Thr with bis(succinimidyl) carbonate in the presence of a catalytic amount of a base affords, in solution or in the solid phase, the corresponding peptides with one or two, consecutive or alternate oxazolidin-2-ones (Oxd).
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Intramolecular reductive ketone-alkynoate coupling reaction promoted by ([small eta] 2-propene)titanium

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07049A, Paper

Christian Schafer, Michel Miesch, Laurence Miesch
Intramolecular reductive coupling of cycloalkanones tethered to alkynoates in the presence of ([small eta]2-propene)titanium was successfully performed to provide hydroxy-esters in a diastereoselective manner. Subsequent lactonization afforded angularly fused unsaturated tricyclic...
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Borondipyrromethene-derived Cu2+ sensing chemodosimeter for fast and selective detection

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06980F, Paper

Chunchang Zhao, peng feng, jian cao, xuezhe wang, yang yang, yulin zhang, jinxin zhang, yanfen zhang
Here, we report a new Cu2+-selective fluorescent turn-on probe BODIPY-EP, in which the 2-pyridinecarboxylic acid is connected to a 6-hydroxyindole-based BODIPY platform through an ester linkage. The ester bond of...
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Molecular Design of Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Application

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06909A, Paper

Md. Masud Parvez, Naoki Haraguchi, Shinichi Itsuno
Chiral polymers containing organocatalyst in their main-chain structure is an important tool for the asymmetric reactions. Reaction of quaternary ammonium halide and sodium sulfonate gives stable salt of quaternary ammonium...
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Understanding Local Electrophilicity/Nucleophilicity Activation through a Single Reactivity Difference Index

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06943A, Paper

Luis R. Domingo, Prof. Pratim K Chattaraj , Soma Duley
A local reactivity difference index Rk is shown to be able to predict the local electrophilic and/or nucleophilic activation within an organic molecule. Together with the electrophilic and/or nucleophilic behavior...
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Aminohydroxyacetone Synthons: Versatile Intermediates for the Organocatalytic Asymmetric Aldol Reaction

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07107J, Paper

Hiyoshizo Kotsuki, Yoshiyuki Komatsu, Riki Watanabe, Keiji Nakano
A practical method for the synthesis of 1,3-aminohydroxyacetone synthons was developed, and their utility in the organocatalytic asymmetric aldol reaction was demonstrated in a short synthesis of aza-sugars.
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Facile Synthesis of 4-Substituted 3,4-Dihydrocoumarins via an Organocatalytic Double Decarboxylation Process

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25075F, Communication

Jian Wang
Over the past few decades, natural products have proven to be useful small-molecule probes in medicinally community.1 A rapid access to small molecules that are guided by natural products appears...
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Highly efficient asymmetric Michael addition of aldehyde to nitrooleﬁn using perhydroindolic acid as a chiral organocatalyst

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB00003B, Paper

Lina Zhao, Jiefeng Shen, Delong Liu, Yangang Liu, Wanbin Zhang
Perhydroindolic acids, the by-products of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-type catalysts are unique for their rigid...
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Copper(I)-amine metallo-organocatalyzed synthesis of carbo- and heterocyclic systems

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06449A, Paper

Benjamin Montaignac, Victor Ostlund, Maxime R. Vitale, Virgnie Ratovelomanana-Vidal, Veronique Michelet
The efficient and atom economical synthesis of 5-membered cyclic structures is achieved through the combination of aminocatalysis and metal catalysis (30 examples 51-96% yield including cyclopentanes, indanes, pyrrolidines and tetrahydrofuran).
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Biological activity of Fe(III) aquo-complexes towards ferric chelate reductase (FCR)

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06754D, Paper

Rosa Escudero, Mar Gomez-Gallego, Santiago Romano, Israel Fernandez, Angel Gutierrez-Alonso, Miguel A. Sierra, Sandra Lopez-Rayo, Paloma Nadal, Juan J. Lucena
Fe(III)-aquo complexes derived from phenol polyaminocarboxylic acids are highly efficient towards the enzyme ferric chelate reductase (FCR) and show interesting structure-activity properties in the enzymatic reduction process.
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Recent advances in the stereoselective synthesis of carbohydrate 2-C-analogs

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06529K, Perspective

Jian Yin, Torsten Linker
A perspective summarizing recent syntheses of carbohydrate 2-C-analogs 1 by ring-opening of cyclopropanated sugars 3 and radical additions to glycals 2 is given.
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Tunnelling control of chemical reactions - The organic chemist's perspective

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07170C, Emerging Area

David Ley, Dennis Gerbig, Peter Schreiner
Even though quantum mechanical tunnelling has been appearing recurrently mostly in theoretical studies that emphasize its decisive role for many chemical reactions, it still appears suspicious to most organic chemists....
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Chiral recognition of carbon nanoforms

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07159B, Emerging Area

Emilio M Perez, Nazario Martin
The selective recognition of chiral carbon nanoforms poses a fundamental challenge. New design principles must be devised to construct hosts capable of enantiodiscrimination between species in which chirality does not...
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A heterotrimetallic Pd/Sm/Pd complex for asymmetric Friedel-Crafts alkylations of pyrroles with nitroalkenes

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25074H, Communication

Guoqi Zhang
Catalytic asymmetric Friedel-Crafts alkylations of pyrroles and nitroalkenes were carried out by using a novel heterotrimetallic Pd/Sm/Pd catalyst based on a simple chiral ligand 1, to give the adducts with...
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Hydrogen tunnelling influences the isomerisation of some small radicals of interstellar importance. A theoretical investigation.

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07102A, Paper

Tianfang Wang, John H Bowie
Hydrogen atom isomerisations within five radical systems (i.e., CH₃^.NH /^.CH₂NH; CH₃O^./^.CH₂OH; ^.CH₂SH / CH₃S^.; CH₃CO₂^. / ^.CH₂CO₂H; and HOCH₂CH₂O^. / HO^.CHCH₂OH) have been studied via quantum-mechanical hydrogen tunnelling through reaction...
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Investigation of the electrophilic reactivity of the cytotoxic marine alkaloid discorhabdin B

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07090A, Paper

Cary Lam, Tanja Grkovic, Norrie Pearce, Brent R. Copp
The mechanisms of action of the cytotoxic marine pyrroloiminoquinone alkaloids the discorhabdins are unknown. We have determined that discorhabdin B acts as an electrophile towards biomimetic thiol nucleophiles leading to...
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High efficiency of superacid HF/SbF5 for the selective decrystallization/depolymerization of cellulose to glucose

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07143F, Communication

Agnes Martin Mingot, Karine Vigier, Francois Jerome, SEBASTIEN THIBAUDEAU
Herein, we show that superacid HF/SbF5 is able after polyprotonation to depolymerise selectively cellulose to water-soluble carbohydrates along with 68 wt% yield of glucose. This process is efficient at low...
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Radical-mediated nitrile translocation as the key step in the stereoselective transformation of 2-(4-chloro-2-cyanobutyl)aziridines to methyl cis-(1-arylmethyl-4-phenylpiperidin-2-yl)acetates

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07062F, Paper

Karel Vervisch, Matthias D'hooghe, Karl W. Tornroos, Norbert De Kimpe
Non-activated 2-(4-chloro-2-cyano-2-phenylbutyl)aziridines were used as building blocks for the stereoselective synthesis of novel cis-2-cyanomethyl-4-phenylpiperidines via a microwave-assisted aziridine to piperidine ring expansion followed by a radical-induced nitrile translocation through initial...
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A highly diastereoselective three-component tandem 1,4-conjugated addition-cyclization reaction to multisubstituted pyrrolidines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06760A, Paper

Xia Zhang, Jingjing Ji, Yingguang Zhu, Changcheng Jing, Ming Li, Wenhao Hu
Three-component reactions of diazoacetophenones with anilines and unsaturated ketoesters afford multisubstituted pyrrolidines in good yield with high diastereoselectivity.
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Characterization of DcsC, a PLP-independent racemase involved in the biosynthesis of D-cycloserine

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06864H, Paper

David Dietrich, Marco J. van Belkum, John C. Vederas
We show that DcsC is a PLP-independent racemase that acts on O-ureidoserine. It is inhibited by cysteine-inactivating reagents such as Hg²⁺, iodoacetamide, and a substrate analogue bearing an epoxide.
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Switching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06708K, Paper

Roslyn Eadie, Craig Richmond, Samantha Moreton, Leroy Cronin
5-(2-bromoethyl)phenanthridinium bromide undergoes a 3-step-one-pot cyclisation reaction with primary amines allowing the facile synthesis of a vast library of heterocycles.
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Antioxidant activity of peptide-based angiotensin converting enzyme inhibitors

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06533A, Paper

Bhaskar J. Bhuyan, Govindasamy Mugesh
It is shown that there is a phenylalanine binding pocket at the angiotensin converting enzyme (ACE) active site. Sec-Pro-Phe tripeptides are better inhibitors of ACE as compared to the Sec-Pro dipeptides. The importance of the sequence of amino acid residues in ACE inhibition is also described. Selenocysteine-based ACE inhibitors can be beneficial for the treatment of hypertension as they are found to possess antioxidant properties.
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An alternative approach: a highly selective dual responding fluoride sensor having active methylene group as binding site

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06815J, Paper

Priyadip Das, Manoj K. Kesharwani, Amal K. Mandal, Eringathodi Suresh, Bishwajit Ganguly, Amitava Das
Active methylene functionality acts as a new binding motif for anions. This reagent is ideally suited as a specific chromogenic sensor for recognition of F^- among all other competitive anions including CN^-, H₂PO₄^- and CH₃CO₂^-. Hydrogen bond formation is the main binding force, however an excess aliquot of F^- triggers deprotonation.
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Highly emissive hand-shaped [small pi]-conjugated alkynylpyrenes: Synthesis, structures, and photophysical properties

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06865F, Paper

Jian-Yong Hu, Xin-Long Ni, Xing Feng, Masanao Era, Mark R. J. Elsegood, Simon J. Teat, Takehiko Yamato
Three hand-shaped, highly fluorescent and stable alkynylpyrenes were successfully designed and synthesized, which are promising candidates in OLED-like optoelectronic devices.
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Trichlorosilane mediated asymmetric reductions of the C[double bond, length as m-dash]N bond

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06854K, Perspective

Simon Jones, Christopher J. A. Warner
Lewis base activated trichlorosilane mediated reduction of ketimines offers significant advantages as an alternative method for the synthesis of chiral amine building blocks.
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Asymmetric synthesis of [small alpha],[small beta]-diamino acid derivatives with an aziridine-, azetidine- and [gamma]-lactone-skeleton via Mannich-type additions across [small alpha]-chloro-N-sulfinylimines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06637H, Paper

Gert Callebaut, Sven Mangelinckx, Lorand Kiss, Reijo Sillanpaa, Ferenc Fulop, Norbert De Kimpe
New chiral syn- and anti-[gamma]-chloro-[small alpha],[small beta]-diamino esters are formed in high yield and in excellent diastereomeric ratios via stereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral [small alpha]-chloro-N-p-toluenesulfinylimine.
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Solid-state supramolecular assemblies consisting of planar charged species

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07059F, Paper

Yohei Haketa, Mayumi Takayama, Hiromitsu Maeda
Pyrrole-based [small pi]-conjugated anion-responsive molecules provided various planar anionic structures by complexation with halide anions, resulting in the formation of solid-state assemblies with planar counter cations and exhibiting various modes of...
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Intramolecular Chiral Communication in Peptide-Dendron Hybrids

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07014F, Communication

Hui Shao, Nicholas A Bewick, Jon Parquette
The conformational properties of a series of peptide-dendron hybrids progressively incorporating 1-4 dendritic side chains were investigated by circular dichroism. Although the presence of multiple adjacent dendrons along the peptide...
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A Computational Study of the Enantioselective Addition of n-BuLi to Benzaldehyde in the Presence of a Chiral Lithium N,P-Amide

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06910E, Paper

Sten O. Nilsson Lill, Per-Ola Norrby, Jurgen Grafenstein, Goran Hilmersson, Petra Ronnholm
In the presence of a chiral lithium N,P amide, alkylation of benzaldehyde results in an enantioselective formation of 1-phenyl-pentanol. This stereoselective addition reaction has herein been studied using dispersion-corrected density...
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Tetrakis(methylimidazole) and tetrakis(methylimidazolium) calix[4]arenes: competitive anion binding and deprotonation

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07025A, Paper

Charlotte E. Willans, Emma K Bullough, Marc A Little, Colin Kilner
Neutral tetrakis(methylimidazole) (1) and the novel cationic tetrakis(methylimidazolium) (2) calixarenes have been prepared and their solid-state and solution behaviour examined. The neutral imidazole forms a mono-zwitterion at elevated temperature, a...
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A NMR AND COMPUTATIONAL STUDY OF SMAC MIMICS TARGETING BOTH THE BIR2 AND BIR3 DOMAINS IN XIAP PROTEIN

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06979B, Paper

Donatella Potenza, laura Belvisi
In this paper we report an extensive NMR analysis of small ligands (Smac mimics) complexed with different constructs of XIAP. The mimics-binding site of XIAP is known as the BIR3...
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Click Synthesized Dianthryl-TTFV: An Efficient Fluorescent Turn-On Probe for Transition Metal Ions

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06828A, Communication

Karimulla Mulla, Prateek Dongare, David W Thompson, Yuming Zhao
Tetrathiafulvalene vinylogue (TTFV) was functionalized with two anthryl fluorophores via Cu(I)-catalyzed alkyne-azide [3+2] cycloaddition, forming a dianthryl-TTFV hybrid to show fluorescent turn-on sensing behaviour for Cu2+, Fe2+, and Cd2+ ions...
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Fused Ring Aziridines as a Facile Entry into Triazole Fused Tricyclic and Bicyclic Heterocycles

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07042A, Paper

Fang Fang, Megan Vogel, Jennifer V Hines, Stephen Bergmeier
The intramolecular dipolar cycloaddition of an azide with an alkyne has provided a useful entry into triazole fused tricyclic heterocycles containing both the triazole ring and the oxazolidin-2-one ring system....
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Synthesis and Protein Binding Studies of a Peptide Fragment of Clathrin Assembly Protein AP180 Bearing an O-Linked b-N-Acetylglucosaminyl-6-phosphate Modification

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07139H, Communication

Richard James Payne, Mark E Graham, Robin S Stone, Phillip J Robinson
A novel post-translational modification of threonine, b-N-acetylglucosaminyl-phosphate, was recently discovered on assembly protein AP180, a protein which plays a crucial role in clathrin coated vesicle formation in synaptic vesicle endocytosis...
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Involvement of DNA binding domain in the cellular stability and importin affinity of NF-[small kappa]B component RelB

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07104E, Paper

Masatoshi Takeiri, Kana Horie, Daisuke Takahashi, Mariko Watanabe, Ryoichi Horie, Siro Simizu, Kazuo Umezawa
NF-[small kappa]B is a transcription factor for the immune activation and tissue stability, but excess activation of NF-[small kappa]B often causes inflammation and cancer. An NF-[small kappa]B component RelB is involved in B-cell...
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A selective fluorescent turn-on NIR probe for cysteine

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07046D, Communication

Xin-Dong Jiang, Jian Zhang, Xiangmin Shao, Weili Zhao
A selective and sensitive turn-on fluorescent NIR probe for cysteine has been developed.
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Concise synthesis of an enantiopure bicyclic pyrazinone as constrained peptidomimetic building block

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06762E, Paper

Vincent Gembus, Solenn Janvier, Jean-Pierre Lecouve, Lucile Vaysse-Ludot, Jean-Francois Briere, Vincent Levacher
A concise synthetic route has been developed for the preparation of a constrained peptidomimetic pyrazinone building block.
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Synthesis of pyrrolyldipyrrinato BF2 complexes by oxidative nucleophilic substitution of boron dipyrromethene with pyrrole

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06689K, Paper

Min Zhang, Erhong Hao, Jinyuan Zhou, Changjiang Yu, Guifeng Bai, Fengyun Wang, Lijuan Jiao
Pyrrolyldipyrrinato BF₂ complexes have been synthesized via a direct oxidative nucleophilic substitution of the 3-hydrogen of BODIPY dyes by pyrrole.
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The dependence of [small alpha]-tocopheroxyl radical reduction by hydroxy-2,3-diarylxanthones on structure and micro-environment

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06612B, Paper

Patrice Morliere, Larry K. Patterson, Clementina M. M. Santos, Artur M. S. Silva, Jean-Claude Maziere, Paulo Filipe, Ana Gomes, Eduarda Fernandes, M. Beatriz Q. Garcia, Rene Santus
Four hydroxyl groups are required for the repair of [small alpha]-tocopheroxyl radical by hydroxy-2,3-diarylxanthones.
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Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06859A, Paper

Esmaeil Sheibani, Kenneth Warnmark
A second generation of supramolecular catalysts has been developed displaying increased substrate selectivity in epoxidations of styrene and stilbene derivatives.
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2-Aminopyrimidine as a novel scaffold for biofilm modulation

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06871K, Paper

Erick A. Lindsey, Roberta J. Worthington, Cristina Alcaraz, Christian Melander
An efficient synthetic route to a series of substituted 2-aminopyrimidine (2-AP) derivatives has been developed. Several derivatives displayed the ability to modulate bacterial biofilm formation, exhibiting greater activity against Gram-positive strains than Gram-negative strains.
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Efficient synthesis of carbazoles via PtCl2-catalyzed RT cyclization of 1-(indol-2-yl)-2,3-allenols: scope and mechanism

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06474F, Paper

Wangqing Kong, Chunling Fu, Shengming Ma
The efficient PtCl₂-catalyzed synthesis of carbazoles from 1-(indol-2-yl)-2,3-allenols through a unique metal carbene intermediate is described.
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Copper(I) Acetate-Catalyzed Azide-Alkyne Cycloaddition for Highly Efficient Preparation of 1-(Pyridin-2-yl)-1,2,3-Triazoles

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06942C, Paper

Qun Zhang, Xinyan Wang, Chuanjie Cheng, Rui Zhu, Nan Liu, Yuefei Hu
A highly efficient copper(I)-catalyzed azide-alkyne cycloaddition of 6-NO2 and 6-CO2Et substituted tetrazolo[1,5-a]pyridines was developed for the preparation of 1-(pyridin-2-yl)-1,2,3-triazoles by simply using copper(I) acetate as a catalyst. The in situ...
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Using Light and a Molecular Switch to 'Lock' and 'Unlock" the Diels-Alder Reaction

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06908C, Paper

Zach Erno, Amir AsadiRad, Vincent Lemieux, Neil R. Branda
Light is used to 'gate' the Diels-Alder reaction using a photoresponsive dithienylfuran backbone and turn the reversibility of the Diels-Alder reaction 'off' and 'on' at 100 [degree]C. These features make...
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Relaxation of the rigid backbone of an oligoamide-foldamer-based [small alpha]-helix mimetic: identification of potent Bcl-xL inhibitors

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07125H, Communication

Jeremy Yap, Xiaobo Cao, Kenno Vanommeslaeghe, Kwan-Young Jung, Paul Wilder, anjan nan, Alex Mackerell, W Roy Smythe, Steven Fletcher
By conducting a structure-activity relationship study of the backbone of a series of oligoamide-foldamer-based [small alpha]-helix mimetics of the Bak BH3 helix, we have identified especially potent inhibitors of Bcl-xL. The...
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Fluorogenic sensing of CH3CO2- and H2PO4- by ditopic receptor through conformational change

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06994F, Paper

Nisar Ahmed, Vangaru Suresh, Bahareh Shirinfar, Inacrist Geronimo, Amita Bist, In-Chul Hwang, Kwang S. Kim
Cyclo-bis-(urea-3,6-dichlorocarbazole) (1) forms a 1 : 2 complex with CH₃CO₂^- and H₂PO₄^- through hydrogen bonding with the two urea moieties, resulting in fluorescence enhancement via a combined photoinduced electron transfer (PET) and energy transfer mechanism.
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Insights into a surprising reaction: The microwave-assisted direct esterification of phosphinic acids

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06972E, Paper

Gyorgy Keglevich, Nora Zsuzsa Kiss, Zoltan Mucsi, Tamas Kortvelyesi
New synthetic results and theoretical data including the thermodynamic and kinetic parameters are discussed for the direct esterification of phosphinic acids that is reluctant on heating, but takes place quantitatively on MW irradiation.
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Pyrazine alkaloids via dimerization of amino acid-derived [small alpha]-amino aldehydes: biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3-indolylmethyl)pyrazine and actinopolymorphol C

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06935K, Paper

Sandhya Badrinarayanan, Jonathan Sperry
The dimerization of amino acid-derived [small alpha]-amino aldehydes provides a short, biomimetic synthesis of several 2,5-disubstituted pyrazine natural products.
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The microbial cell factory

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06903B, Perspective

Cormac D. Murphy
Microorganisms are involved in many applications; this review outlines some of the contemporary products arising from manipulation of bacteria and fungi.
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Studies on a novel class of triaryl pyridine N-glycosylamine amphiphiles as super gelators

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06834F, Paper

Manivannan Kalavathi Dhinakaran, Thangamuthu Mohan Das
A novel class of six different triaryl pyridine N-glycosylamine amphiphiles was synthesised and characterized based on different spectral techniques, such as NMR and mass analysis. Gelation was observed predominantly in aliphatic solvents and is due to the presence of the alkyl chain. All the gels thus obtained were studied using powder XRD and FE-SEM techniques which reveal fibrous entanglement of the molecules in the gel state.
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Lipothiophosphoramidates for gene delivery: critical role of the cationic polar headgroup

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06812E, Paper

Aurore Fraix, Tristan Montier, Tony Le Gall, Charlotte M. Sevrain, Nathalie Carmoy, Mattias F. Lindberg, Pierre Lehn, Paul-Alain Jaffres
The synthesis of cationic lipothiophosphoramidates possessing different cationic groups (ammonium, phosphonium or arsonium) is reported. Transfection experiments showed that the arsonium-containing lipid (Z⁺ = As⁺) is globally the most efficient on the three cell lines tested.
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Mechanism of the alkali degradation of (6-4) photoproduct-containing DNA

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06966K, Paper

Norihito Arichi, Aki Inase, Sachise Eto, Toshimi Mizukoshi, Junpei Yamamoto, Shigenori Iwai
The mechanism of the alkali-induced strand breaks caused at the (6-4) photoproduct sites in UV-irradiated DNA was elucidated.
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Investigating the Reaction Mechanism and Organocatalytic Synthesis of [small alpha],[small alpha]'-Dihydroxy Ketones

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06939C, Paper

Helen Hailes, James L Galman, David Steadman, Lisa D Haigh
A biomimetic TK one-pot reaction using hydroxypyruvate and aldehydes to generate [small alpha],[small alpha]'-dihydroxy ketones in water has recently been described. To investigate this tertiary-amine mediated reaction mechanism two approaches were used....
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A General Electron Transfer Reduction of Lactones Using SmI2-H2O

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB00017B, Communication

Michal Szostak, Karl D Collins, Neal J Fazakerley, Malcolm Spain, David John Procter
Herein we describe a strategy for the selective, electron transfer reduction of lactones of all ring sizes and topologies using SmI2-H2O and a Lewis base to tune the redox properties...
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A New Synthetic Route for Axially Chiral Secondary Amines with Binaphthyl Backbone and Their Applications in Asymmetric Michael Reaction of Aldehydes to Nitroalkenes

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07110J, Paper

Da-Cheng Liang, Ren-Shi Luo, Li-Hua Yin, Albert S. C. Chan, Gui Lu
A new synthetic route for binaphthyl-based secondary amines has been developed. The key feature of this route includes the selective direct esterification of the binaphthyl structure at the 3- or...
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One-pot sequential Ti- / Cu-catalysis for tandem amidation/Ullmann-type cyclization: synthesis of model benzodiazepine(di)ones promoted by microwave irradiation

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07063D, Paper

Leonardo Ciofi, Andrea Trabocchi, Claudia Lalli, Gloria Menchi, Antonio Guarna
The application of sequential Ti- / Cu-catalysis in the model one-pot synthesis of benzodiazepine(di)ones promoted by microwave irradiation demonstrates the expediency of dual catalysis in coupling-cyclization methods useful for applications...
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N-Activated [small beta]-lactams as versatile reagents for acyl carrier protein labeling

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06846J, Paper

Gitanjeli Prasad, Jon W. Amoroso, Lawrence S. Borketey, Nathan A. Schnarr
A series of reactive [small beta]-lactams have been prepared for direct labeling of holo-acyl carrier proteins in site-selective fashion.
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Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06644K, Paper

Sunil V. Pansare, Eldho K. Paul
The enantioselective synthesis of 2,3-disubstituted piperidines was achieved by employing an organocatalytic direct vinylogous aldol reaction as the key step.
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Synthesis of amine-functionalized heparin oligosaccharides for the investigation of carbohydrate-protein interactions in microtiter plates

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06607F, Paper

Susana Maza, Giuseppe Macchione, Rafael Ojeda, Javier Lopez-Prados, Jesus Angulo, Jose L. de Paz, Pedro M. Nieto
A series of amine-functionalized heparin oligosaccharides were efficiently synthesized and attached to microplates for the qualitative and quantitative analysis of their interactions with proteins.
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Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB25065A, Paper

Shaojun Zheng, Luca Laraia, Cornelius O' Connor, David Sorrell, Zhaochao Xu, Ashok Venkitaraman, Wenjun Wu, David Spring
A novel synthesis of the ellagitannin natural product Tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to...
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The direct catalytic asymmetric aldol reaction of [small alpha]-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07193B, Communication

Seiji Shirakawa, Kensuke Ota, Shogo J. Terao, Keiji Maruoka
Enantioselective direct aldol reaction of [small alpha]-substituted nitroacetates with aqueous formaldehyde for the synthesis of [small alpha]-alkyl serines has been achieved under base-free neutral phase-transfer conditions with a bifunctional chiral phase-transfer catalyst.
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Syntheses of (-)-Pelletierine and (-)-Homopipecolic Acid.

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06984A, Communication

Wen-Hua Chiou, Guei-Tang Chen, Chien-Lun Kao, Yu-Kai Gao
Enantiomerical syntheses of (-)-homopipecolic acid and (-)-pelletierine have been achieved by chiral resolution of tropanol followed by Baeyer Villiger oxidation. The methodology provides a practical route for syntheses of optically...
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Bismuth(III) triflate promoted intramolecular hydroamination of unactivated alkenyl sulfonamides in the preparation of pyrrolidines

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07064B, Paper

Frantisek Mathia, Peter Szolcsanyi
Bi(OTf)3.nH2O was found to be an efficient promoter of the cyclisative hydroamination of unactivated alkenyl sulfonamides, giving rise to the N-protected 2-methyl pyrrolidines in good to excellent yields (up to...
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One-pot preparation of piperazines by regioselective ring-opening of non-activated arylaziridines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07099E, Communication

Piera Trinchera, Biagia Musio, Leonardo Degennaro, Anna Moliterni, Aurelia Falcicchio, Renzo Luisi
A new straightforward synthesis of 2,5-disubstituted N,N-dialkylpiperazines starting from non-activated N-alkyl arylaziridines and a catalytic amount of Lewis acid is reported.
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Resorcinarene bis-crown silver complexes and their application as antibacterial Langmuir-Blodgett films

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06920B, Paper

Kaisa Helttunen, Negar Moridi, Patrick Shahgaldian, Maija Nissinen
Antibacterial coatings based on LB films of supramolecular resorcinarene bis-crown Ag(I) complex inhibit E. coli growth with only nanomolar Ag⁺ concentration.
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New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06695E, Paper

Sara Soto, Esther Vaz, Carmela Dell'Aversana, Rosana Alvarez, Lucia Altucci, Angel R. de Lera
New paullones, synthesized by a one-pot Suzuki-Miyaura intramolecular amidation, strongly inhibited hSIRT-1 and induced granulocyte differentiation of the U937 leukemia cell line.
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The conformers of 3-fluoroalanine. A theoretical study

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06492H, Paper

Ionel Humelnicu, Ernst-Ulrich Wurthwein, Gunter Haufe
The relative energies (kcal mol^-1) of 3-fluoroalanine conformers in the gas phase and in water were calculated (DFT, SCS-MP2) and compared to those of alanine.
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Bioinspired Organocatalytic Asymmetric Reactions

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07037E, Perspective

Alfredo Ricci, Luca Bernardi, Mariafrancesca Fochi, Mauro Comes Franchini
Several small organic molecule catalysts reminds natural enzymes in their mode of action and substrate interaction/activation. This striking similarity has been a great source of inspiration for the development of...
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Intramolecular proton transfer impact on antibacterial properties of ansamycin antibiotic rifampicin and its new amino analogues

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB00008C, Communication

Krystian Pyta, Piotr Przybylski, Barbara Wicher, Maria Gdaniec, Joanna Stefanska
Tautomerisation of rifampicin (1) and its 2-9 analogues has been indicated by 1H, 13C and 15N NMR and X-ray studies. Biological data with structural analysis of interactions at RNAP binding...
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One-step synthesis of differently bis-functionalized isoxazoles by cycloaddition of carbamoylnitrile oxide with [small beta]-keto esters

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06925C, Paper

Nagatoshi Nishiwaki, Kazuya Kobiro, Shotaro Hirao, Jun Sawayama, Kazuhiko Saigo, Yumiko Ise, Maho Nishizawa, Masahiro Ariga
Carbamoylnitrile oxide underwent inverse electron-demand 1,3-dipolar cycloaddition with 1,3-dicarbonyl compounds in the presence of magnesium acetate to afford bis-functionalized isoxazoles.
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TBD/Al2O3: a novel catalytic system for dynamic intermolecular aldol reactions that exhibit complex system behaviour

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06648C, Paper

Angel Martinez-Castaneda, Humberto Rodriguez-Solla, Carmen Concellon, Vicente del Amo
The catalytic system TBD/Al₂O₃ allows the preparation of thermodynamically-controlled pools of aldols, interconverting through an aldol/retro-aldol sequence, from which moderate levels of diastereoselectivity can emerge.
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Chemical generation of o-quinone monoimines for the rapid construction of 1,4-benzoxazine derivatives

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06681E, Communication

Naganjaneyulu Bodipati, Rama Krishna Peddinti
Highly reactive o-benzoquinone monoimines were chemically generated by the oxidation of o-aminophenols with diacetoxyiodobenzene and successfully trapped with electron-rich vinylic ethers or thioethers to synthesize novel 1,4-benzoxazine derivatives.
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Synthesis of N-substituted [varepsilon]-hexonolactams as pharmacological chaperones for the treatment of N370S mutant Gaucher disease

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06987C, Communication

Guan-Nan Wang, Gabriele Twigg, Terry D. Butters, Siwei Zhang, Liangren Zhang, Li-He Zhang, Xin-Shan Ye
A series of novel N-substituted [varepsilon]-hexonolactams were prepared efficiently using a tandem ring-expansion reaction as the key step. Some synthetic compounds showed better enhancements to N370S mutant [small beta]-glucocerebrosidase activity than NB-DNJ and NN-DNJ.
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Fungal biofilm inhibitors from a human oral microbiome-derived bacterium

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06856G, Paper

Xiaoru Wang, Lin Du, Jianlan You, Jarrod B. King, Robert H. Cichewicz
Mutanobactins from an oral-cavity-derived bacterium offer insight into how the human microbiome may afford protection against disease.
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Carbazole-thiosemicarbazone-Hg(II) ensemble-based colorimetric and fluorescence turn-on toward iodide in aqueous media and its application in live cell imaging

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06792G, Paper

Ajit Kumar Mahapatra, Jagannath Roy, Prithidipa Sahoo, Subhra Kanti Mukhopadhyay, Amarnath Chattopadhyay
A carbazole-thiosemicarbazone-Hg²⁺ ensemble-based fluorogenic probe for detection of iodide in aqueous media is reported. The practical use of an 'ensemble' was demonstrated by its application to the detection of iodide in the living cells.
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Formation of new base pairs between inosine and 5-methyl-2-thiocytidine derivatives

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06641F, Paper

Akihiro Ohkubo, Yudai Nishino, Yu Ito, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
DNA and 2[prime or minute]-OMe-RNA probes containing 5-methyl-2-thiocytidine (m⁵s²C) residues that can bind selectively and strongly to the corresponding RNA targets containing inosine residues by the significant stacking effect and steric hindrance of the 2-thiocarbonyl group are reported.
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Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06898B, Paper

Thorfinnur Gunnlaugsson, J M Kelly, Jonathan Kitchen, Swagata Banerjee
The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and...
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One-pot synthesis of a piperidine-based rigidified DTPA analogue and its bifunctional chelating agent.

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07154A, Communication

Lorenzo Tei, Gabriele Alessandro Rolla, Giuseppe Gugliotta, Mauro Botta
The core structure of cis-3,5-diaminopiperidine was N-alkylated with excess t-butylbromoacetate in order to exploit the successive N-quaternarization and Stevens rearrangement to access at the same time the pentaalkylated product and...
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Diversity-Oriented Derivatization of BODIPY Based on Regioselective Bromination

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07004A, Communication

Yongzhou Hu, Xin Li, Shufang Huang
Regioselectively brominated BODIPYs were shown to undergo nucleophilic substitution and Sonogashira coupling reactions with a one-pot procedure, yielding diversely substituted fluorophores.
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A Stereospecific Synthesis of 2,3,5,6-Tetrasubstituted Tetrahydropyrans via (3,5)-Oxonium-Ene Reaction

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06832J, Paper

Anil Saikia, Pipas Saha, Anup Bhunia
An efficient method for the synthesis of 2,3,5,6-tetrasubstituted tetrahydropyrans has been developed from the reaction of aldehydes and ethyl 2-(1-hydroxyalkyl/hydroxy(phenyl)methyl)-5-methylhex-4-enoate using (3,5)-oxonium-ene reaction promoted by boron trifluoride etherate in good...
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Helix and Hairpin Nucleation in Short Peptides Using Centrally Positioned Conformationally Constrained Dipeptide Segments[dagger]

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06817F, Paper

S Chandrappa, S Aravinda, S Ragothama, Rajesh Sonti, RAJKISHOR RAI, Veldore V Harini, N shamala, P Balaram
The effect of incorporation of a centrally positioned Ac₆c-Xxx segment where Xxx = ^LVal / ^DVal into a host oligopeptide composed of L-amino acid residues has been investigated. Studies of...
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Accurate Prediction of Rate Constants of Diels-Alder Reactions and Application to Design of Diels-Alder Ligation

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07079K, Paper

Shiya Tang, Jing Shi, Qingxiang Guo
Bioorthorgonal reactions are useful tools to gain insights into the structure, dynamics, and function of biomolecules in the field of chemical biology. Recently, Diels-Alder reaction is a promising and attractive...
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"Sulfolefin": Highly modular mixed S/Olefin ligands for enantioselective Rh-catalyzed 1,4-addition

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB07132K, Communication

Noureddine Khiar, Alvaro Salvador, Ahmed Chelouan, Ana Alcudia, Inmaculada Fernandez
Sulfolefins I obtained in one step from DAG-sulfinate esters are excellent catalysts for the Rh-catalyzed 1,4-addition of boronic acids to cyclic and acyclic olefins.
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Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06434K, Paper

Zhi-Ming Zhou, Zhi-Huai Li, Xiao-Yan Hao, Jun Zhang, Xiao Dong, Ying-Qiang Liu, Wen-Wen Sun, Dan Cao, Jin-Liang Wang
C ₂ -symmetric imidazolium-tagged bis(oxazoline) ligands were prepared, with an ee of up to 94%, and the catalyst could be reused 6 times without loss of activity/enantioselectivity.
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C2-symmetric Proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB06897D, Paper

Yongmei Wang
A C2-symmetric tetraamine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding adducts 1,5-dicarbonyl compounds were obtained in good chemical yields with high levels of...
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Efficient Syntheses of 2, 3-Disubstituted Natural Quinazolinones via Iridium Catalysis

Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB07178A, Communication

Jianguang Zhou, Jie Fang
Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis.
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Palladium-catalyzed three-component reaction of 2-alkynylbromobenzene, 2-alkynylaniline, and electrophile: an efficient pathway for the synthesis of diverse 11H-indeno[1,2-c]quinolines

Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06764A, Paper

Xiaolin Pan, Yong Luo, Jie Wu
Diverse 11H-indeno[1,2-c]quinolines are produced via a palladium-catalyzed three-component reaction of 2-alkynylbromobenzene, 2-alkynylaniline, and electrophile.
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