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An international journal for the quickest publication of high-quality research covering the breadth of synthetic, physical and biomolecular organic chemistry.
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Issue 11 of OBC
15 May 2008
Find out more about this issue's covers, Perspective, Emerging Area and hot articles.
Hot Paper: Bright future for functional molecules
07 May 2008
Molecules can display display logic, sense, numeracy and utility and communicate with humans using light signals.
Surprise reaction degrades chemical weapons
30 April 2008
Australian scientists improve our understanding of how peroxides destroy chemical warfare agents.
Previous news stories
Contents list for Organic & Biomolecular Chemistry, issue 11, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 1857
DOI: 10.1039/b807359g
Inside front cover
Org. Biomol. Chem., 2008, 6, 1858
DOI: 10.1039/b807360k
Contents and Chemical Biology
Org. Biomol. Chem., 2008, 6, 1859
DOI: 10.1039/b807361a
Emerging Area
Chiral ferrocenes as novel rotary modules for molecular machines
Kazushi Kinbara, Takahiro Muraoka and Takuzo Aida,
Org. Biomol. Chem., 2008, 6, 1871
DOI: 10.1039/b718982f
Ferrocene, a double-decker organometallic compound that generates angular motion, can be used as a unique rotary module for molecular machines.
Perspective
Modulating the electronic properties of porphyrinoids: a voyage from the violet to the infrared regions of the electromagnetic spectrum
Yannick Rio, M. Salomé Rodríguez-Morgade and Tomás Torres,
Org. Biomol. Chem., 2008, 6, 1877
DOI: 10.1039/b800617b
The accomplishments achieved so far in the porphyrinoid area relating to the absorption wavelengths of its different members, and the possibility of preparing novel systems with different colour properties and, consequently, new emerging applications, are discussed.
Communications
Epigenetic remodeling of the fungal secondary metabolome
Russell B. Williams, Jon C. Henrikson, Ashley R. Hoover, Andrlynn E. Lee and Robert H. Cichewicz,
Org. Biomol. Chem., 2008, 6, 1895
DOI: 10.1039/b804701d
Fungi treated with DNA methyltransferase and histone deacetylase inhibitors exhibit natural product profiles with enhanced chemical diversity demonstrating that small-molecule epigenetic modifiers are effective tools for rationally controlling the native expression of fungal biosynthetic pathways and generating new biomolecules.
Phenylenediamine catalysis of 
click glycosylations
in water: practical and direct access to unprotected neoglycoconjugates
Aurélie Baron, Yves Blériot, Matthieu Sollogoub and Boris Vauzeilles,
Org. Biomol. Chem., 2008, 6, 1898
DOI: 10.1039/b805528a
Phenylenediamine-catalyzed click chemistry leads to the efficient, practical, and column-free preparation of neoglycoconjugates from unprotected glucosyl azide, in pure water when aglycon solubility permits.
Regio- and stereocontrolled synthesis of novel 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines from 2-(bromomethyl)- or 2-(sulfonyloxymethyl)aziridines
Michinori Karikomi, Matthias D'hooghe, Guido Verniest and Norbert De Kimpe,
Org. Biomol. Chem., 2008, 6, 1902
DOI: 10.1039/b804246m
A highly efficient regio- and stereocontrolled synthesis of 3-sulfonamido-2,3,4,5-tetrahydro-1,5-benzothiazepines has been accomplished starting from easily accessible aziridine substrates.
Papers
Dendronised block copolymers as potential vectors for gene transfection
Tony J. Wigglesworth, Francisco Teixeira Jr. , Fabian Axthelm, Sara Eisler, Noemi S. Csaba, Hans P. Merkle, Wolfgang Meier and François Diederich,
Org. Biomol. Chem., 2008, 6, 1905
DOI: 10.1039/b802808g
The modular synthesis of block copolymers bearing a dendronised cationic block for DNA complexation and a poly(ethylene glycol) block for encapsulation of the complex is reported. These materials strongly complex DNA and spontaneously form polyion complex micelles in the presence of plasmid DNA.
Identification of a novel 
-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A
Wai-Ho Lam, Kathrin Rychli and Timothy D. H. Bugg,
Org. Biomol. Chem., 2008, 6, 1912
DOI: 10.1039/b802585a
A pyridoxal 5
-phosphate dependent enzyme activity has been identified, that is responsible for conversion of L-threonine and ammonia into 2,3-diaminobutyric acid in Streptomyces flavidovirens.
Nonenzymic polycyclisation of analogues of oxidosqualene with a preformed C-ring
Johan M. Winne, Pierre J. De Clercq, Marco Milanesio, Philip Pattison and Davide Viterbo,
Org. Biomol. Chem., 2008, 6, 1918
DOI: 10.1039/b801670d
Enhanced HTML article available
Cationic polycyclisations of partially constrained epoxypolyenes are reported, aspects of which bear interesting analogies with their biosynthetic counterparts involved in sterol formation.
Manipulation of an intramolecular NH
O hydrogen bond by photoswitching between stable E/Z isomers of the cinnamate framework
Takashi Matsuhira, Hitoshi Yamamoto, Taka-aki Okamura and Norikazu Ueyama,
Org. Biomol. Chem., 2008, 6, 1926
DOI: 10.1039/b719960k
An intramolecular NHO hydrogen bond was switched by E/Z photoisomerization of the cinnamate framework; the pKa value of the carboxylic acid was decreased by using 313 nm photoirradiation.
Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl terminal bis(butadiynes) (HC
C–CC–Ar–CC–CCH) and their applications in the synthesis of oligo(arylenebutadiynylene) molecular wires
Kara West, Changsheng Wang, Andrei S. Batsanov and Martin R. Bryce,
Org. Biomol. Chem., 2008, 6, 1934
DOI: 10.1039/b802968g
Terminal aryl/heteroaryl bis(butadiynes) (HC–C
C–CC–Ar–CC–CCH) have been isolated and exploited in the synthesis of highly-conjugated oligo(arylenebutadiynylene)s.
A new approach to anodic substitution reaction using acoustic emulsification
Ryosuke Asami, Toshio Fuchigami and Mahito Atobe,
Org. Biomol. Chem., 2008, 6, 1938
DOI: 10.1039/b802961j
Anodic oxidation of the substrate successfully proceeded without affecting the oxidation of nucleophile and the carbocation generated was rapidly trapped by the coexisting electro-inactive nucleophile droplets before its decomposition.
A cyclic RGD-coated peptide nanoribbon as a selective intracellular nanocarrier
Yong-beom Lim, Oh-Joon Kwon, Eunji Lee, Pyung-Hwan Kim, Chae-Ok Yun and Myongsoo Lee,
Org. Biomol. Chem., 2008, 6, 1944
DOI: 10.1039/b802470g
A -ribbon coated with cyclic Arg-Gly-Asp (cRGD) can encapsulate hydrophobic guest molecules, and deliver them into cells selectively.
Hydroindation of allenes and its application to radical cyclization
Naoki Hayashi, Yusuke Hirokawa, Ikuya Shibata, Makoto Yasuda and Akio Baba,
Org. Biomol. Chem., 2008, 6, 1949
DOI: 10.1039/b803314e
Hydroindation of allenes and radical cyclization of 1,2,7-trienes (allenenes) were accomplished by HInCl2 with high regioselectivity to afford a variety of vinylic indiums which could be used for successive coupling reactions in a one-pot procedure.
Cucurbit[7]uril host–guest complexes of the histamine H2-receptor antagonist ranitidine
Ruibing Wang and Donal H. Macartney,
Org. Biomol. Chem., 2008, 6, 1955
DOI: 10.1039/b801591k
The histamine H2-receptor antagonist ranitidine forms very stable complexes with the cucurbit[7]uril molecule in aqueous solution over a wide pH range, reducing its acidity and increasing its thermal stability.
The aerobic oxidation of alcohols with a ruthenium porphyrin catalyst in organic and fluorinated solvents
Vasily N. Korotchenko, Kay Severin and Michel R. Gagné,
Org. Biomol. Chem., 2008, 6, 1961
DOI: 10.1039/b800583d
Under appropriate activation conditions fluorinated ruthenium porphyrin complexes catalyze the aerobic oxidation of non-enolizable alcohols. Experiments to distinguish between auto-oxidation and metal catalysis are reported.
Exciplex and excimer molecular probes: detection of conformational flip in a myo-inositol chair
Manikandan Kadirvel, Biljana Arsic, Sally Freeman and Elena V. Bichenkova,
Org. Biomol. Chem., 2008, 6, 1966
DOI: 10.1039/b800710a
Green fluorescence of exciplex and excimer containing myo-inositol orthoesters is lost upon acid-induced deprotection to give penta-equatorial chairs with blue fluorescence. This ring flip provides an irreversible switch for the development of acid-sensitive fluorescent probes.
Intermediates in the reduction of the antituberculosis drug PA-824, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine, in aqueous solution
Robert F. Anderson, Sujata S. Shinde, Andrej Maroz, Maruta Boyd, Brian D. Palmer and William A. Denny,
Org. Biomol. Chem., 2008, 6, 1973
DOI: 10.1039/b801859f
Stepwise reduction of the nitroimidazole moiety in aqueous solution proceeds atypically at the imidazole ring followed by the nitro group.
A stereodivergent synthesis of -hydroxy-
-methylene lactones via vinyl epoxides
Marion Davoust, Frédéric Cantagrel, Patrick Metzner and Jean-François Brière,
Org. Biomol. Chem., 2008, 6, 1981
DOI: 10.1039/b802310g
The sulfonium ylide epoxidation of aldehydes furnished novel vinyl epoxides, which served as useful building blocks for a stereodivergent route towards -hydroxy--methylene lactones. A formal synthesis of the antibiotic conocandin, displaying this vinyl oxirane motif, is also described.
Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin
Jon Deeley, Anna Bertram and Gerald Pattenden,
Org. Biomol. Chem., 2008, 6, 1994
DOI: 10.1039/b802477d
Synthetic approaches to the contiguously linked poly-azole units and to the macrocycles in telomestatin and YM-216391 are described. The synthetic cyclopeptide YM-216391 is shown to be the enantiomer of the natural product isolated from Streptomyces nobilis.
An enantioselective approach to (+)-laurencin
Vikrant A. Adsool and Sunil V. Pansare,
Org. Biomol. Chem., 2008, 6, 2011
DOI: 10.1039/b803973a
A concise enantioselective synthesis of an advanced intermediate for the marine natural product (+)-laurencin is described. Ring-opening of an ephedrine-derived spiro-epoxide, hemiacetal allylation and ring closing metathesis are the key steps in the synthesis.
Back matter
Org. Biomol. Chem., 2008, 6, 2016
DOI: 10.1039/b807362g
Back cover
Org. Biomol. Chem., 2008, 6, 2019
DOI: 10.1039/b807363p
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