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Contents list for Organic & Biomolecular Chemistry, issue 23, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 4273
DOI: 10.1039/b819244h
Inside front cover
Org. Biomol. Chem., 2008, 6, 4274
DOI: 10.1039/b819245f
Contents and Chemical Biology
Org. Biomol. Chem., 2008, 6, 4275
DOI: 10.1039/b819246b
Communications
Hyperstable miniproteins: additive effects of D- and L-Ala mutations
D. Victoria Williams, Bipasha Barua and Niels H. Andersen,
Org. Biomol. Chem., 2008, 6, 4287
DOI: 10.1039/b814314e
The effects of alanine substitutions in each helical segment of the structure, and Gly to D-Ala mutations at sites where glycines have positive 
angles in the Trp-cage miniprotein are reported. The effects of stabilizing mutations are additive, yielding a 20-residue construct (Tm = 83 °C). The preference for a D-Ala can be as large as 16 kJ mol-1.
A simple assay to probe disease-associated enzyme activity using glycosaminoglycan-assisted synthesized gold nanoparticles
Zhihui Ban, Carlos J. Bosques and Ram Sasisekharan,
Org. Biomol. Chem., 2008, 6, 4290
DOI: 10.1039/b813210k
Template-assisted synthesis of gold nanoparticles with glycosaminoglycans is reported. The potential of using the scaffolds to measure the activity of disease-associated enzymes in a simple assay is also illustrated.
Stereoselective synthesis of the hormonally active (25S)-
7-dafachronic acid, (25S)-4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid
René Martin, Frank Däbritz, Eugeni V. Entchev, Teymuras V. Kurzchalia and Hans-Joachim Knölker,
Org. Biomol. Chem., 2008, 6, 4293
DOI: 10.1039/b815064h
We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.
Highly diastereo- and enantioselective construction of both central and axial chiralities by Rh-catalyzed [2 + 2 + 2] cycloaddition
Takanori Shibata, Mayumi Otomo, Yu-ki Tahara and Kohei Endo,
Org. Biomol. Chem., 2008, 6, 4296
DOI: 10.1039/b814014f
An intermolecular [2 + 2 + 2] cycloaddition of enynes, possessing an ortho-substituted aryl group, with bulky acetylenedicarboxylates proceeded to give bicyclic cyclohexa-1,3-dienes with both central and axial chiralities in an extremely highly diastereo- and enantioselective manner.
Papers
Stereoselective aziridination of cyclic allylic alcohols using chloramine-T
Susannah C. Coote, Peter O'Brien and Adrian C. Whitwood,
Org. Biomol. Chem., 2008, 6, 4299
DOI: 10.1039/b811137e
The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored and cis-stereoselectivity generally predominated.
Enzymes containing porous polymersomes as nano reaction vessels for cascade reactions
Suzanne M. Kuiper, Madhavan Nallani, Dennis M. Vriezema, Jeroen J. L. M. Cornelissen, Jan C. M. van Hest, Roeland J. M. Nolte and Alan E. Rowan,
Org. Biomol. Chem., 2008, 6, 4315
DOI: 10.1039/b811196k
Herein we report on the encapsulation and protection of glucose oxidase (GOx) and horse radish peroxidase (HRP) inside porous PS-PIAT polymersomes and the successful employment of these functionalised nanoreactors in a cascade reaction.
Novel pH indicator dyes for array preparation via NHS ester activation or solid-phase organic synthesis
Sabine Trupp, Patrick Hoffmann, Thomas Henkel and Gerhard J. Mohr,
Org. Biomol. Chem., 2008, 6, 4319
DOI: 10.1039/b814683g
An immobilised pH-sensitive indicator shows increases in fluorescence at decreasing pH, yielding a pKa around 6.8 with excitation at 400 and emission at around 520 nm.
Photo-control of peptide conformation on a timescale of seconds with a conformationally constrained, blue-absorbing, photo-switchable linker
Andrew A. Beharry, Oleg Sadovski and G. Andrew Woolley,
Org. Biomol. Chem., 2008, 6, 4323
DOI: 10.1039/b810533b
A photo-switch is reported that isomerizes from trans to cis when irradiated at 400 nm and relaxes in the dark with a half-life of 
1 s. The photo-switch can be used to reversibly alter the helical content of peptides.
Isolation, structure elucidation and total synthesis of a cytotoxic dienone from Echinacea pallida
Stefania Morandi, Federica Pellati, Claudia Ori, Barbara Adinolfi, Paola Nieri, Stefania Benvenuti and Fabio Prati,
Org. Biomol. Chem., 2008, 6, 4333
DOI: 10.1039/b812700j
In this paper, chromatographic and spectroscopic techniques, combined with total synthesis, were successfully applied to the isolation and structure elucidation of a cytotoxic dienone from E. pallida roots, namely (8Z,11Z)-pentadeca-8,11-dien-2-one.
Rhodium catalysed conjugate addition of a chiral alkenyltrifluoroborate salt: the enantioselective synthesis of hermitamides A and B
Christopher G. Frost, Stephen D. Penrose and Robert Gleave,
Org. Biomol. Chem., 2008, 6, 4340
DOI: 10.1039/b812897a
The concise enantioselective synthesis of hermitamides A and B is presented utilising a rhodium catalysed conjugate addition reaction to introduce the side chain and chiral information in a single step via an alkenyltrifluoroborate salt.
Development of a method for the parallel synthesis and purification of N-substituted pantothenamides, known inhibitors of coenzyme A biosynthesis and utilization
Marianne van Wyk and Erick Strauss,
Org. Biomol. Chem., 2008, 6, 4348
DOI: 10.1039/b811086g
We present a simple method for the parallel synthesis and purification of N-substituted pantothenamides—known inhibitors of coenzyme A biosynthesis and utilization—and demonstrate its potential and utility by evaluating a small library of these compounds as bacterial growth inhibitors.
Chemistry and folding of photomodulable peptides – stilbene and thioaurone-type candidates for conformational switches
Máté Erdélyi, Miranda Varedian, Christian Sköld, Ida B. Niklasson, Johanna Nurbo, Ĺsa Persson, Jonas Bergquist and Adolf Gogoll,
Org. Biomol. Chem., 2008, 6, 4356
DOI: 10.1039/b812001c
Synthetic strategies for the preparation of photoswitchable molecular scaffolds with stilbene or thioaurone chromophores, and their incorporation into peptidomimetics, are presented.
Structure-activity relationship study of CXCR4 antagonists bearing the cyclic pentapeptide scaffold: identification of the new pharmacophore
Tomohiro Tanaka, Hiroshi Tsutsumi, Wataru Nomura, Yasuaki Tanabe, Nami Ohashi, Ai Esaka, Chihiro Ochiai, Jun Sato, Kyoko Itotani, Tsutomu Murakami, Kenji Ohba, Naoki Yamamoto, Nobutaka Fujii and Hirokazu Tamamura,
Org. Biomol. Chem., 2008, 6, 4374
DOI: 10.1039/b812029c
Design of cyclic pentapeptide libraries based on structure-activity relationship data of CXCR4 anatgonists led to development of novel lead compounds to find new pharmacophore moieties.
Molecular recognition through divalent interactions with a self-assembled fibrillar network of a supramolecular organogel
Beatriu Escuder, Juan F. Miravet and José A. Sáez,
Org. Biomol. Chem., 2008, 6, 4378
DOI: 10.1039/b812520a
The self-assembled fibrillar network of a supramolecular gel affords arrays of H-bond acceptor pyridine groups capable of selective interaction with resorcinol over other phenol derivatives. The interaction is very conveniently monitored by NMR relaxometry.
Theoretical studies on the carcinogenic activity of diol epoxide derivatives of PAH: proton affinity and aromaticity as decisive descriptors
K. Periya Vijayalakshmi and Cherumuttathu H. Suresh,
Org. Biomol. Chem., 2008, 6, 4384
DOI: 10.1039/b813008f
A multifaceted approach consisting of molecular electrostatic potential analysis, proton affinity calculations, MO analysis, and NICS(1)zz based aromaticity calculations has been utilized to explore the high carcinogenic activity of bay-region diol epoxide derivatives of polycyclic aromatic hydrocarbons.
Controlling the direction of site-selectivity and regioselectivity in RNA ligation by Zn2+-dependent deoxyribozymes that use 2
,3-cyclic phosphate RNA substrates
Diana M. Kost, Joseph P. Gerdt, P. I. Pradeepkumar and Scott K. Silverman,
Org. Biomol. Chem., 2008, 6, 4391
DOI: 10.1039/b813566e
The site-selectivity and regioselectivity of forming various RNA linkages by Zn2+-dependent deoxyribozymes were explored. Specific design aspects of the selection strategy favor synthesis of native 3-5 RNA linkages.
Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C
Tohru Taniguchi, Kenji Monde, Koji Nakanishi and Nina Berova,
Org. Biomol. Chem., 2008, 6, 4399
DOI: 10.1039/b813437e
Chiral sulfinates have been studied by theoretical calculations of optical rotation, ECD and VCD. The absolute configuration of a sulfinic cruciferous phytoalexin, brassicanal C, has been conveniently and reliably assigned by this approach.
Tandem addition-cyclization reactions of 2-alkynylbenzenamines with isocyanates catalyzed by PdCl2
Shengqing Ye, Qiuping Ding, Zhiyong Wang, Haibo Zhou and Jie Wu,
Org. Biomol. Chem., 2008, 6, 4406
DOI: 10.1039/b812015c
Tandem addition-cyclization reactions of 2-alkynylbenzenamines with isocyanates catalyzed by palladium chloride gave rise to 1,2-disubstituted indoles in good yields.
Targeting DNA with 
light-up
pyrimidine triple-helical forming oligonucleotides conjugated to stabilizing fluorophores (LU-TFOs)
Brice-Loďc Renard, Rémy Lartia and Ulysse Asseline,
Org. Biomol. Chem., 2008, 6, 4413
DOI: 10.1039/b813289e
LU-TFOs are labelled with a series of cyanine monomethines. Conjugates able to form triplexes without loss of specificity together with a strong fluorescence enhancement have been selected.
Directed epoxidation of cyclohexa-1,4-dienes–stereoselective formation of up to six contiguous stereogenic centres
Michael Butters, Dirk J. Beetstra, Mark C. Elliott, Joseph Hill-Cousins and Benson M. Kariuki,
Org. Biomol. Chem., 2008, 6, 4426
DOI: 10.1039/b814131m
Seven examples: stereoselective formation of five and six contiguous stereogenic centres.
Synthesis of 1-hydroperoxy-1-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers
Alexander O. Terent'ev, Maxim M. Platonov, Igor B. Krylov, Vladimir V. Chernyshev and Gennady I. Nikishin,
Org. Biomol. Chem., 2008, 6, 4435
DOI: 10.1039/b809661a
It was found that iodine-catalyzed reactions of geminal bishydroperoxides with acetals proceed with the replacement of only one alkoxy group by the peroxide group to give 1-hydroperoxy-1
-alkoxyperoxides in yields up to 64%.
Alcohol cross-coupling reactions catalyzed by Ru and Ir terpyridine complexes
Dinakar Gnanamgari, Chin Hin Leung, Nathan D. Schley, Sheena T. Hilton and Robert H. Crabtree,
Org. Biomol. Chem., 2008, 6, 4442
DOI: 10.1039/b815547j
Primary alcohols can be coupled with secondary benzylic alcohols by an air-stable catalytic system involving terpyridine ruthenium or iridium complexes.
Antiplasmodial, 
-haematin inhibition, antitrypanosomal and cytotoxic activity in vitro of novel 4-aminoquinoline 2-imidazolines
Chitalu C. Musonda, Vanessa Yardley, Renata C. Carvalho de Souza, Kanyile Ncokazi, Timothy J. Egan and Kelly Chibale,
Org. Biomol. Chem., 2008, 6, 4446
DOI: 10.1039/b813007h
A novel series of 4-aminoquinoline-containing 2-imidazolines were synthesized via a one-pot 3-component condensation reaction and evaluated against two strains of the malaria parasite Plasmodium falciparum and one strain of trypanosomal parasite Trypanosoma brucei.
Synthesis of 3-(carboxyarylalkyl)imidazo[2,1-f][1,2,4]triazines as potential inhibitors of AMP deaminase
Joseph K. Kirkman, Stephen D. Lindell, Simon Maechling, Alexandra M. Z. Slawin and Christopher J. Moody,
Org. Biomol. Chem., 2008, 6, 4452
DOI: 10.1039/b810850a
The design and synthesis of potential inhibitors of AMP deaminase, incorporating an imidazotriazine ring as an adenine mimic and a carboxyalkylaryl moiety as a ribose phosphate mimic, is described.
Synthesis of Gd(III)-C-palmitamidomethyl-C-DOTAMA-C6-o-carborane: a new dual agent for innovative MRI/BNCT applications
Silvio Aime, Alessandro Barge, Antonella Crivello, Annamaria Deagostino, Roberto Gobetto, Carlo Nervi, Cristina Prandi, Antonio Toppino and Paolo Venturello,
Org. Biomol. Chem., 2008, 6, 4460
DOI: 10.1039/b808804g
A bifunctionalised carborane incorporating a very lipophilic palmitil chain and a Gd(III)-DOTA complex has been synthesised, allowing the quantitative determination of boron in cells.
Back cover
Org. Biomol. Chem., 2008, 6, 4467
DOI: 10.1039/b819247m
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