_tcm18-11415.gif )
Latest News
2008 OBC lecture award presented
24 June 2008
Akimitsu Okamoto receives his OBC lecture award at the 31st National Medicinal Chemistry Symposium in Pittsburgh
Highest ever impact factor for OBC
20 June 2008
Newly released ISI citation data show that OBC's Impact Factor has risen by over 10%.
Previous news stories
Contents list for Organic & Biomolecular Chemistry, issue 14, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 2445
DOI: 10.1039/b810385m
Inside front cover
Org. Biomol. Chem., 2008, 6, 2446
DOI: 10.1039/b810386k
Contents and Chemical Science
Org. Biomol. Chem., 2008, 6, 2447
DOI: 10.1039/b810387a
Emerging Area
Molecular imprinting of proteins emerging as a tool for protein recognition
Toshifumi Takeuchi and Takayuki Hishiya,
Org. Biomol. Chem., 2008, 6, 2459
DOI: 10.1039/b715737c
Receptor-like synthetic materials such as molecularly imprinted polymers for proteins have been intensively studied as substitutes for natural receptors and recent developments in protein imprinting demonstrate potential for the future technology of protein recognition.
Perspective
Bright molecules with sense, logic, numeracy and utility
A. Prasanna de Silva, Thomas P. Vance, Matthew E. S. West and Glenn D. Wright,
Org. Biomol. Chem., 2008, 6, 2468
DOI: 10.1039/b802963f
Fluorophores (F), spacers (S), receptors (R), and accessory modules can be organized into systems that can switch their fluorescence from 
off
to on for various applications in information handling.
Communications
First total synthesis of clausine L and pityriazole, a metabolite of the human pathogenic yeast Malassezia furfur
Ronny Forke, Anne Jäger and Hans-Joachim Knölker,
Org. Biomol. Chem., 2008, 6, 2481
DOI: 10.1039/b805451g
Enhanced HTML article available
The first total synthesis of the alkaloid pityriazole is described using three consecutive palladium-catalyzed coupling reactions.
Facile synthesis of novel indolo[3,2-b]carbazole derivatives and a chromogenic-sensing 5,12-dihydroindolo[3,2-b]carbazole
Rong Gu, Koen Robeyns, Luc Van Meervelt, Suzanne Toppet and Wim Dehaen,
Org. Biomol. Chem., 2008, 6, 2484
DOI: 10.1039/b807255h
Novel indolo[3,2-b]carbazole derivatives and a chromogenic-sensing 5,12-dihydroindolo[3,2-b]carbazole have been synthesized starting from tetra-tert-butylated 6,12-diaryl-5,11-dihydroindolo[3,2-b]carbazoles, which were prepared via an efficient tert-butylation of 6,12-diaryl-5,11-dihydroindolo[3,2-b]carbazoles.
Combining multi-catalysis and multi-component systems for the development of one-pot asymmetric reactions: stereoselective synthesis of highly functionalized bicyclo[4.4.0]decane-1,6-diones
Dhevalapally B. Ramachary and Rajasekar Sakthidevi,
Org. Biomol. Chem., 2008, 6, 2488
DOI: 10.1039/b806243a
We have developed a direct amine/acid-catalyzed stereoselective hydrogenation of a variety of Wieland–Miescher ketones, Hajos–Parrish ketones and their analogs with Hantzsch esters as the hydrogen source. This approach was used to construct highly functionalized chiral bicyclo[4.4.0]decane-1,6-diones.
Papers
O-Allyl protection in the Fmoc-based synthesis of difficult PNA
Frank Altenbrunn and Oliver Seitz,
Org. Biomol. Chem., 2008, 6, 2493
DOI: 10.1039/b805165h
The use of O-allyl-protected thymine Fmoc-tAll facilitated the solid-phase synthesis of difficult homothymine PNA-oligomers, even in cases where the use of non-protected thymine building blocks resulted in 70% truncation products. Deallylation occurs during the TFA cleavage step. Thus, O-allyl-protection can be applied in combination with standard protocols used in automated PNA synthesis.
Carbonic anhydrase inhibitors. Sulfonamide diuretics revisited—old leads for new applications?
Claudia Temperini, Alessandro Cecchi, Andrea Scozzafava and Claudiu T. Supuran,
Org. Biomol. Chem., 2008, 6, 2499
DOI: 10.1039/b800767e
Sulfonamide diuretics, known to moderately inhibit carbonic anhydrase II, were shown to strongly inhibit other CA isozymes. The crystal structure of CA II–indapamide shows that this compound binds in a manner not seen before for any CA inhibitor.
Towards sequence selective DNA binding: design, synthesis and DNA binding studies of novel bis-porphyrin peptidic nanostructures
Eric Biron and Normand Voyer,
Org. Biomol. Chem., 2008, 6, 2507
DOI: 10.1039/b803281e Enhanced HTML article available
A new series of peptidic nanostructures bearing two cationic porphyrins was designed and synthesized to achieve selective recognition of DNA sequences via bis-intercalation.
Photoresponsive peptoid oligomers bearing azobenzene side chains
Neel H. Shah and Kent Kirshenbaum,
Org. Biomol. Chem., 2008, 6, 2516
DOI: 10.1039/b804802a
N-Substituted glycine peptoid oligomers were synthesized to incorporate a photoresponsive azobenzene side chain, and the reversible photoisomerization and cis- to trans-azobenzene thermal isomerization of this side chain were studied.
A rationalization of the solvent effect on the Diels–Alder reaction in ionic liquids using multiparameter linear solvation energy relationships
Riccardo Bini, Cinzia Chiappe, Veronica Llopsis Mestre, Christian Silvio Pomelli and Thomas Welton,
Org. Biomol. Chem., 2008, 6, 2522
DOI: 10.1039/b802194e
The Diels–Alder reaction between cyclopentadiene and three dienophiles has been investigated in ionic liquids and molecular solvents, and the solvent effects on selectivity and reactivity have been examined using multiparameter linear solvation energy relationships.
Experimental determination of the gas phase proton affinities of the conjugate base anions of 2-iodoxybenzoic acid (IBX) and 2-iodosobenzoic acid (IBA)
Tom Waters, Jack Boulton, Timothy Clark, Michael J. Gallen, Craig M. Williams and Richard A. J. O'Hair,
Org. Biomol. Chem., 2008, 6, 2530
DOI: 10.1039/b803452d
The gas-phase proton affinities of the conjugate base anions of the organic oxidant 2-iodoxybenzoic and its reduced form 2-iodosobenzoic acid were examined using mass-spectrometry based experiments and theoretical calculations.
Porphyrin–naphthodiimide interactions as a structural motif in foldamers and supramolecular assemblies
Zulkifli Merican, Ken D. Johnstone and Maxwell J. Gunter,
Org. Biomol. Chem., 2008, 6, 2534
DOI: 10.1039/b804267e
– Charge-transfer interactions between naphthalenediimides (NDI) and porphyrins (POR) are shown to be prevalent in linked NDI–POR and POR–NDI–POR structures, leading to foldamers in flexible structures.
The Sharpless asymmetric aminohydroxylation reaction: optimising ligand/substrate control of regioselectivity for the synthesis of 3- and 4-aminosugars
Jennifer A. Bodkin, George B. Bacskay and Malcolm D. McLeod,
Org. Biomol. Chem., 2008, 6, 2544
DOI: 10.1039/b803310b
An understanding of substrate–catalyst interactions in the Sharpless asymmetric aminohydroxylation reaction unlocks avenues for the enantioselective synthesis of naturally occurring and regioisomeric 3- and 4-aminosugar derivatives.
Mono- and dicationic short PEG and methylene dioxyalkylglycerols for use in synthetic gene delivery systems
Christopher A. Hurley, John B. Wong, Jimmy Ho, Michele Writer, Scott A. Irvine, M. Jayne Lawrence, Stephen L. Hart, Alethea B. Tabor and Helen C. Hailes,
Org. Biomol. Chem., 2008, 6, 2554
DOI: 10.1039/b719702k Enhanced HTML article available
Novel monocationic and dicationic cytofectins have been synthesised possessing hydrophobic and hydrophilic linkers for formulation into lipopolyplex transfection vectors.
Dependence of product formation from decomposition of nitroso-dithiols on the degree of nitrosation. Evidence that dinitroso-dithiothreitol acts solely as an nitric oxide releasing compound
Sonja Liebeskind, Hans-Gert Korth, Herbert de Groot and Michael Kirsch,
Org. Biomol. Chem., 2008, 6, 2560
DOI: 10.1039/b801583j
It is shown that the degree of nitrosation of dithiols determines the yield of nitric oxide and of nitroxyl, respectively.
Efficient stereoselective nucleophilic addition of pyrroles to chiral nitrones
Christophe Berini, Frédéric Minassian, Nadia Pelloux-Léon, Jean-Noël Denis, Yannick Vallée and Christian Philouze,
Org. Biomol. Chem., 2008, 6, 2574
DOI: 10.1039/b802997k
Efficient regioselective additions of pyrroles to optically active nitrones under smooth acidic conditions leads to chiral pyrrolic N-hydroxylamines. Application to the stereoselective synthesis of pyrrolic amino acids is described.
Synthesis of polyhydroxy piperidines and their analogues: a novel approach towards selective inhibitors of 
-glucosidase
Ganesh Pandey, Kishor Chandra Bharadwaj, M. Islam Khan, K. S. Shashidhara and Vedavati G. Puranik,
Org. Biomol. Chem., 2008, 6, 2587
DOI: 10.1039/b804278k
Various polyhydroxy piperidine azasugars, including their amine analogues, have been synthesized, many of which show selective and potent inhibition of -glucosidases.
Propensity for local folding induced by the urea fragment in short-chain oligomers
Lucile Fischer, Claude Didierjean, Franck Jolibois, Vincent Semetey, Jose Manuel Lozano, Jean-Paul Briand, Michel Marraud, Romuald Poteau and Gilles Guichard,
Org. Biomol. Chem., 2008, 6, 2596
DOI: 10.1039/b801139g
The propensity for intramolecular H-bonding has been compared in short-chain aza analogues of 
- and 
-amino acid derivatives. Whereas a urea-turn is largely populated in the first series, nearest-neighbour H-bonded interactions become unfavourable in higher homologues.
Concise synthesis of the tricyclic core of lycoposerramine S
Mark C. Elliott, Nahed N. E. El Sayed and James S. Paine,
Org. Biomol. Chem., 2008, 6, 2611
DOI: 10.1039/b804664f Enhanced HTML article available
The first entirely synthetic approach to the lycoposerramine alkaloids is reported. A symmetrical cyclohexa-1,4-diene precursor is desymmetrised to form the key quaternary stereogenic centre, and the core is complete using an iodocyclisation.
Stereochemistry and rearrangement reactions of hydroxylignanolactones
Barbara Raffaelli, Monika Pohjoispää, Tapio Hase, Christine J. Cardin, Yu Gan and Kristiina Wähälä,
Org. Biomol. Chem., 2008, 6, 2619
DOI: 10.1039/b801593g
The rearrangement mechanisms of various substituted hydroxylignanolactones are investigated under different reaction conditions, and the absolute stereochemistry of some lignano-9,7
-lactones is determined and discussed.
Further studies on silatropic carbonyl ene cyclisations: -crotyl(diphenyl)silyloxy aldehyde substrates; synthesis of 2-deoxy-2-C-phenylhexoses
Jeremy Robertson, Stuart P. Green, Michael J. Hall, Andrew J. Tyrrell and William P. Unsworth,
Org. Biomol. Chem., 2008, 6, 2628
DOI: 10.1039/b804752a
Silatropic carbonyl ene cyclisation is used as a key step in the stereoselective synthesis of 2-deoxy-2-C-phenyl hexose isomers.
Back matter
Org. Biomol. Chem., 2008, 6, 2636
DOI: 10.1039/b810390a
Back cover
Org. Biomol. Chem., 2008, 6, 2639
DOI: 10.1039/b810391g
RSS feed