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Contents list for Organic & Biomolecular Chemistry, issue 15, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 2641
DOI: 10.1039/b811280k
Contents and Chemical Biology
Org. Biomol. Chem., 2008, 6, 2643
DOI: 10.1039/b811281a
Perspective
The tert-butyl group in chemistry and biology
Philippe Bisel, Loay Al-Momani and Michael Müller,
Org. Biomol. Chem., 2008, 6, 2655
DOI: 10.1039/b800083b
The tert-butyl group: a tree from which chemistry has harvested a large crop. But isn't there much more to learn from Nature with regard to possible applications to biocatalytic processes?
Communications
Enzymatic N-methylaminoacylation of tRNA using chemically misacylated AMP as a substrate
Shinsuke Sando, Hiroki Masu, Chika Furutani and Yasuhiro Aoyama,
Org. Biomol. Chem., 2008, 6, 2666
DOI: 10.1039/b806965d
Using 
chemically misacylated AMP
which is photogeneratable, tRNA can be enzymatically acylated with N-methylamino acids with an efficiency comparable to that of the corresponding natural aminoacylation process with amino acids.
The azaquinone-methide elimination: comparison study of 1,6- and 1,4-eliminations under physiological conditions
Rotem Erez and Doron Shabat,
Org. Biomol. Chem., 2008, 6, 2669
DOI: 10.1039/b808198k
The 1,4- and the 1,6-azaquinone-methide eliminations are powerful and efficient reactions useful for the disassembly of spacers in prodrug systems.
Stereoselective desymmetrisation of prochiral 
,-dicyanoalkenes via domino Michael–Michael addition reactions
Tai-Ran Kang, Jian-Wu Xie, Wei Du, Xin Feng and Ying-Chun Chen,
Org. Biomol. Chem., 2008, 6, 2673
DOI: 10.1039/b809308c
The desymmetrisation of prochiral ,-dicyanoalkenes via tandem Michael–Michael addition reactions with ,
-unsaturated ketones, catalysed by 9-amino-9-deoxyepicinchona alkaloids, was investigated.
A new type of self-supported, polymeric Ru-carbene complex for homogeneous catalysis and heterogeneous recovery: synthesis and catalytic activities for ring-closing metathesis
Shu-Wei Chen, Ju Hyun Kim, Hyunik Shin and Sang-gi Lee,
Org. Biomol. Chem., 2008, 6, 2676
DOI: 10.1039/b809025d
A novel 2nd Grubbs-type catalyst tethering a styrene has been synthesized and automatically polymerized in solution to form a self-supported polymeric Ru-carbene complex, which catalyzed RCM homogeneously, but was recovered heterogeneously.
Papers
An efficient synthesis of triazolo-carbohydrate mimetics and their conformational analysis
Hikaru Yanai, Shun Obara and Takeo Taguchi,
Org. Biomol. Chem., 2008, 6, 2679
DOI: 10.1039/b803924k
A chemical library of 1,2,3-triazolo-carbohydrate mimetics was constructed. In this synthesis, an In(OTf)3-catalyzed tandem azidation–1,3-dipolar cycloaddition reaction of 1,1-dimethoxyhex-5-ynes with TMSN3 was used as the key step to construct the 7-alkoxy-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine framework.
Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers
Firoz A. Jaipuri and Nicola L. Pohl,
Org. Biomol. Chem., 2008, 6, 2686
DOI: 10.1039/b803451f
The first synthesis of linear and branched mannose oligosaccharides using fluorous-tag assistance is reported with reagents and fluorous solid-phase extraction (FSPE) protocols that are amenable to automation.
Reagent switchable stereoselective (1,2) mannoside mannosylation: OH-2 of mannose is a privileged acceptor
Katie J. Doores and Benjamin G. Davis,
Org. Biomol. Chem., 2008, 6, 2692
DOI: 10.1039/b803999m
Enhanced HTML article available
The discovery of novel conditions for highly -stereoselective (>9 : 1) mannosylation of OH-2 of mannosides using a straightforward perbenzylthioglycoside donor has allowed ready assembly of -mannosyl oligosaccharides including the repeating trisaccharide motif of the O5 antigen of pathogen Klebsiella pneumoniae.
Layer-by-layer deposition of molecular oligoelectrolytes—investigation of assembling and degradation behaviour
Karin Rosenlehner, Torsten Schunk, Norbert Jux, Michael Brettreich and Andreas Hirsch,
Org. Biomol. Chem., 2008, 6, 2697
DOI: 10.1039/b804290j
Self assembled multilayer films of charged molecular oligoelectrolytes assembled by layer-by-layer deposition (OEMs) were systematically investigated using optical spectroscopy. Both the assembly and disassembly of the OEMs was observed by chromophoric reporter electrolytes. For the first time we have investigated the degradation behavior of OEMs.
2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents
Palwinder Singh, Anu Mittal, Satwinderjeet Kaur, Wolfgang Holzer and Subodh Kumar,
Org. Biomol. Chem., 2008, 6, 2706
DOI: 10.1039/b803608j
2,3-Diaryltetrahydrofurans with an ethylsulfanyl methyl substituent at C-5 exhibit remarkable COX-2 inhibition and growth inhibitory activities at various cancer cell lines.
Antioxidant activity of (+)-bergenin—a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae)
Heitor A. De Abreu, Izandina Aparecida dos S. Lago, Gilmar P. Souza, Dorila Piló-Veloso, Hélio A. Duarte and Antônio Flávio de C. Alcântara,
Org. Biomol. Chem., 2008, 6, 2713
DOI: 10.1039/b804385j
(+)-Bergenin—isolated from a vegetable species found in the Amazon region—exhibits strong antioxidant activity. The mechanism of its free radical scavenging ability is elucidated.
Inhibitors of the kinase IspE: structure–activity relationships and co-crystal structure analysis
Anna K. H. Hirsch, Magnus S. Alphey, Susan Lauw, Michael Seet, Luzi Barandun, Wolfgang Eisenreich, Felix Rohdich, William N. Hunter, Adelbert Bacher and François Diederich,
Org. Biomol. Chem., 2008, 6, 2719
DOI: 10.1039/b804375b Enhanced HTML article available
Inhibitors of the kinase IspE from the non-mevalonate pathway, developed using structure-based design, are presented. Structure–activity relationships and a co-crystal structure confirm the proposed binding mode.
The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
Christophe Morin, Tatiana Besset, Jean-Claude Moutet, Martine Fayolle, Margit Brückner, Danièle Limosin, Katja Becker and Elisabeth Davioud-Charvet,
Org. Biomol. Chem., 2008, 6, 2731
DOI: 10.1039/b802649c
The ability of aza-naphthoquinone analogues of both 1,4-naphthoquinone and menadione to act as substrates of Plasmodium falciparum glutathione and thioredoxin reductases and of human erythrocyte glutathione reductase was evidenced in accordance with redox potential values.
Docking, synthesis, and NMR studies of mannosyl trisaccharide ligands for DC-SIGN lectin
José J. Reina, Irene Díaz, Pedro M. Nieto, Nuria E. Campillo, Juan A. Páez, Georges Tabarani, Franck Fieschi and Javier Rojo,
Org. Biomol. Chem., 2008, 6, 2743
DOI: 10.1039/b802144a
NMR (STD and tr-NOE) and computational (docking) studies provide useful information about the recognition of mannosyl di- and trisaccharides by DC-SIGN. This information could assist to the design of new ligands with important biological implications.
Synthesis of aryl-substituted 2-pyridyl-1,10-phenanthrolines; a series of oriented terpyridine analogues
Jeremy K. Klosterman, Anthony Linden and Jay S. Siegel,
Org. Biomol. Chem., 2008, 6, 2755
DOI: 10.1039/b804106g
A 3 × 3 matrix of manisyl (4-methoxy-2,6-dimethylphenyl) substituted pyridyl-1,10-phenanthrolines has been synthesized by utilizing a general palladium catalyzed cross-coupling procedure. The directionality of these terdentate ligands will generate chiral octahedral ML2 complexes, useful for the metal templated synthesis of topologically chiral structures.
Trachycladindoles A–G: cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer
Robert J. Capon, Chongsheng Peng and Cedric Dooms,
Org. Biomol. Chem., 2008, 6, 2765
DOI: 10.1039/b803455a
A southern Australian marine sponge, Trachycladus laevispirulifer, has yielded a family of novel indole-2-carboxylic acids incorporating a rare 2-amino-dihydroimidazole moiety, displaying potent and selective activity against a panel of human cancer cell lines, and representing a new anticancer pharmacophore.
Preparation of leukotriene B4 inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells
Mari Kuramoto, Yoko Sakata, Kumi Terai, Ikuo Kawasaki, Jun-ichi Kunitomo, Takahiro Ohishi, Takehiko Yokomizo, Seiichi Takeda, Shuichi Tanaka and Yoshitaka Ohishi,
Org. Biomol. Chem., 2008, 6, 2772
DOI: 10.1039/b803313g
The preparation of 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their leukotriene B4 inhibitory activity and growth inhibitory activity to human pancreatic cancer cells are described.
A concise and straightforward total synthesis of (±)-salinosporamide A, based on a biosynthesis model
Nicholas P Mulholland, Gerald Pattenden and Iain A. S. Walters,
Org. Biomol. Chem., 2008, 6, 2782
DOI: 10.1039/b803818j
A total synthesis of (±)-salinosporamide, based on a diastereoselective intramolecular aldolisation of a -keto amide intermediate, leading to the pyrrolidinone ring in the natural product, as the key (biomimetic) step, is described.
Direct chlorination of alcohols with chlorodimethylsilane catalyzed by a gallium trichloride/tartrate system under neutral conditions
Makoto Yasuda, Kenji Shimizu, Satoshi Yamasaki and Akio Baba,
Org. Biomol. Chem., 2008, 6, 2790
DOI: 10.1039/b804589e
The reaction of secondary alcohols with chlorodimethylsilane proceeded in the presence of a catalytic amount of GaCl3/diethyl tartrate to give the corresponding organic chlorides.
Kinetic resolution of esters via metal catalyzed methanolysis reactions
Christopher I. Maxwell, Kalpa Shah, Pavel V. Samuleev, Alexei A. Neverov and R. Stan Brown,
Org. Biomol. Chem., 2008, 6, 2796
DOI: 10.1039/b805236k
Abs vs. time plot for the methanolysis of D-Boc-Gln-OPNP and racemic Boc-Gln-OPNP promoted by Pyr-R,R
-chxn:Yb3+:0.5NaOCH3 from which one can calculate the rate constant for decomposition of both D and L isomers.
Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines
Andreas Schmidt, Dirk Michalik, Sven Rotzoll, Ehsan Ullah, Christine Fischer, Helmut Reinke, Helmar Görls and Peter Langer,
Org. Biomol. Chem., 2008, 6, 2804
DOI: 10.1039/b804139c
Densely functionalized azoxabicyclo[3.3.1]nonanones were prepared based on the reaction of 1,1-bis(silyloxy)ketene acetals with isoquinolinium and quinolinium salts.
Generation and hetero-Diels–Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals
Christopher D. Bray,
Org. Biomol. Chem., 2008, 6, 2815
DOI: 10.1039/b806593d
Deprotonation of o-hydroxybenzyl acetate with iPrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2
partners in hetero-Diels–Alder reactions.
Development of a practical Buchwald–Hartwig amine arylation protocol using a conveniently prepared (NHC)Pd(R-allyl)Cl catalyst
Mark J. Cawley, F. Geoffrey N. Cloke, Richard J. Fitzmaurice, Stuart E. Pearson, James S. Scott and Stephen Caddick,
Org. Biomol. Chem., 2008, 6, 2820
DOI: 10.1039/b801479e
(SIPr)Pd(methallyl)Cl 1 is a reliable, easily obtained and shelf-stable catalyst for the arylation of primary and secondary amines with aryl bromides, chlorides and triflates in the presence of lithium hexamethyldisilazide.
Back matter
Org. Biomol. Chem., 2008, 6, 2826
DOI: 10.1039/b811282g
Back cover
Org. Biomol. Chem., 2008, 6, 2827
DOI: 10.1039/b811283p
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