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Contents list for Organic & Biomolecular Chemistry, issue 6, 2008
Front cover
Org. Biomol. Chem., 2008, 6, 941
DOI: 10.1039/b802983k
Inside front cover
Org. Biomol. Chem., 2008, 6, 942
DOI: 10.1039/b802984a
Contents and Chemical Science
Org. Biomol. Chem., 2008, 6, 943
DOI: 10.1039/b802985g
Emerging Area
Is vanadium a more versatile target in the activity of primordial life forms than hitherto anticipated?
Dieter Rehder,
Org. Biomol. Chem., 2008, 6, 957
DOI: 10.1039/b717565p
Enhanced HTML article available
Bacterial recourse to vanadate in respiration (shown), the use of vanadium in nitrogen fixation and, perhaps, nitrate reduction, and generation of a plethora of halogenated organic compounds by marine algae depending on vanadate-dependent haloperoxidases hint towards a more general role of vanadium in earlier life forms.
Perspective
Thiol cofactors for selenoenzymes and their synthetic mimics
Bani Kanta Sarma and Govindasamy Mugesh,
Org. Biomol. Chem., 2008, 6, 965
DOI: 10.1039/b716239a Enhanced HTML article available
Molecular recognition and effective binding of the thiol cofactors at the active site of the selenoenzymes play crucial roles in the catalytic activity. This Perspective highlights the various thiol cofactor systems used by three major selenoenzymes and their synthetic mimics.
Communications
Auxotrophic-precursor directed biosynthesis of nonribosomal lipopeptides with modified tryptophan residues
Bagher Amir-Heidari, Jenny Thirlway and Jason Micklefield,
Org. Biomol. Chem., 2008, 6, 975
DOI: 10.1039/b718766c Enhanced HTML article available
A precursor-directed biosynthesis approach, using a Trp-auxotrophic strain of Streptomyces coelicolor, is described, which enables the introduction of modified tryptophan residues into the calcium-dependent lipopeptide antibiotics (CDAs).
de novo Design and synthesis of N-benzylanilines as new candidates for VEGFR tyrosine kinase inhibitors
Masaharu Uno, Hyun Seung Ban, Wataru Nabeyama and Hiroyuki Nakamura,
Org. Biomol. Chem., 2008, 6, 979
DOI: 10.1039/b719959g Enhanced HTML article available
N-Benzylanilines were designed and synthesized as vascular endothelial growth factor (VEGF)-2 inhibitors using de novo drug design systems based on the X-ray structure of VEGFR-2 kinase domain.
Metastable tert-butylcalix[6]arene with unusually large tunable free volume for non-threshold enclathration of volatiles
Alexey V. Yakimov, Marat A. Ziganshin, Aidar T. Gubaidullin and Valery V. Gorbatchuk,
Org. Biomol. Chem., 2008, 6, 982
DOI: 10.1039/b800187a Enhanced HTML article available
A metastable material with tunable free volume of molecular size, vapor sorption properties of a porous sorbent and variable thermal stability was prepared from tert-butylcalix[6]arene.
A novel efficient and versatile route to the synthesis of 5-O-feruloylquinic acids
Candice Menozzi Smarrito, Caroline Munari, Fabien Robert and Denis Barron,
Org. Biomol. Chem., 2008, 6, 986
DOI: 10.1039/b719132d Enhanced HTML article available
A novel synthesis of 5-O-feruloylquinic acid, a polyphenolic compound found in coffee beans, and its methyl ester derivative has been achieved in a 6 step sequence. This efficient route is the first one that could be applied to the synthesis of human metabolites of chlorogenic acids.
Facile one-pot synthesis of 5-substituted hydantoins
Ross G. Murray, David M. Whitehead, Franck Le Strat and Stuart J. Conway,
Org. Biomol. Chem., 2008, 6, 988
DOI: 10.1039/b719675j
A novel synthesis of 5-substituted and 5,5-disubstituted hydantoins using a one-pot, gallium(III) triflate-catalysed procedure that is compatible with a range of substrates and solvents has been developed.
Efficient palladium-catalyzed synthesis of 3-aryl-4-indolylmaleimides
Anahit Pews-Davtyan, Annegret Tillack, Stefanie Ortinau, Arndt Rolfs and Matthias Beller,
Org. Biomol. Chem., 2008, 6, 992
DOI: 10.1039/b719160j
Improved palladium catalysts for the Suzuki coupling of 3-bromo-1-methyl-4-(2-methyl-3-indolyl)maleimide have been developed. The resulting products are closely related to biologically active 3,4-bisindolylmaleimides.
Papers
Guest exchange in dimeric capsules formed by tetra-urea calix[4]arenes
Ivan Vatsouro, Ellen Alt, Myroslav Vysotsky and Volker Böhmer,
Org. Biomol. Chem., 2008, 6, 998
DOI: 10.1039/b719053k
The rate of guest exchange (benzene vs. the solvent cyclohexane) in hydrogen bonded dimers of tetra-urea calix[4]arenes varies by more than three orders of magnitude for different ether residues.
Cyclic triureas—synthesis, crystal structures and properties
Denys Meshcheryakov, Françoise Arnaud-Neu, Volker Böhmer, Michael Bolte, Véronique Hubscher-Bruder, Emilie Jobin, Iris Thondorf and Sabine Werner,
Org. Biomol. Chem., 2008, 6, 1004
DOI: 10.1039/b718114k
The four possible macrocyclic triureas from diamino xanthene and the more flexible diamino diphenyl ether were prepared; their affinity towards anions was studied by 1H NMR, single crystal X-ray diffraction, UV spectrophotometry and molecular modelling.
Solubilisation of [60]fullerenes using block copolymers and evaluation of their photodynamic activities
Motofusa Akiyama, Atsushi Ikeda, Takashi Shintani, Yuki Doi, Jun-ichi Kikuchi, Takuya Ogawa, Keiichiro Yogo, Tatsuo Takeya and Naoyuki Yamamoto,
Org. Biomol. Chem., 2008, 6, 1015
DOI: 10.1039/b719671g
Block copolymer micelle-incorporated C60 with a cationic surface delivered C60 into HeLa cells and showed cytotoxicity under photoirradiation.
A ratiometric optical imaging probe for intracellular pH based on modulation of europium emission
Robert Pal and David Parker,
Org. Biomol. Chem., 2008, 6, 1020
DOI: 10.1039/b718993a
A cell permeable macrocyclic Eu(III) complex incorporating an N-methylsulfonamide moiety switches the coordination environment at Eu with pH and allows ratiometric pH measurements by spectroscopy or microscopy in the range 6 to 8, following excitation at 384 nm.
Simple and facile synthesis of tetralone-spiro-glutarimides and spiro-bisglutarimides from Baylis–Hillman acetates
Deevi Basavaiah and Raju Jannapu Reddy,
Org. Biomol. Chem., 2008, 6, 1034
DOI: 10.1039/b717843c Enhanced HTML article available
A simple and convenient synthesis of di(E)-arylidene-tetralone-spiro-glutarimides from Baylis–Hillman acetates via an interesting biscyclization strategy involving facile C–C and C–N bond formation is described. Also, one-pot multistep transformation of the Baylis–Hillman acetates into di(E)-arylidene-spiro-bisglutarimides is presented.
Palladium-catalyzed synthesis of indene derivatives via propargylic carbonates with in situ generated organozinc compounds
Zheng-Hui Guan, Zhi-Hui Ren, Lian-Biao Zhao and Yong-Min Liang,
Org. Biomol. Chem., 2008, 6, 1040
DOI: 10.1039/b719957k Enhanced HTML article available
The palladium-catalyzed carboannulation and arylation reaction of propargylic carbonates with in situ generated organozinc compounds produced an important new class of indene derivatives.
Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study
L. M. T. Frija, I. V. Khmelinskii, C. Serpa, I. D. Reva, R. Fausto and M. L. S. Cristiano,
Org. Biomol. Chem., 2008, 6, 1046
DOI: 10.1039/b718104c
The photochemistry of 5-allyloxy-tetrazoles in solution was studied by product analysis and laser flash photolysis. The exclusive primary photochemical process identified was molecular nitrogen elimination, with formation of 1,3-oxazines.
Preparation and purification of 5
-amino-5-deoxyguanosine-5-N-phosphoramidate and its initiation properties with T7 RNA polymerase
David Williamson and David R. W. Hodgson,
Org. Biomol. Chem., 2008, 6, 1056
DOI: 10.1039/b717896d
5-Amino-5-deoxyguanosine-5-N-phosphoramidate (GNHP) was synthesised in four steps from guanosine. GNHP was found to initiate T7 RNAP-promoted transcriptions to afford 5-GNHP-RNA, which hydrolyzes readily to yield 5-H2N-RNA that can be conjugated to activated esters.
Efficient cleavage of the N–O bond of 3,6-dihydro-1,2-oxazines mediated by some 
-hetero substituted carbonyl compounds in mild conditions
Gilles Galvani, Géraldine Calvet, Nicolas Blanchard and Cyrille Kouklovsky,
Org. Biomol. Chem., 2008, 6, 1063
DOI: 10.1039/b718787d
The first purely organic and general 
NO bond cleavage!
Enols and thioenols of substituted cyanomonothiocarbonylmalonamides: structures, enolization vs. thioenolization, equilibria and conformations
Ahmad Basheer and Zvi Rappoport,
Org. Biomol. Chem., 2008, 6, 1071
DOI: 10.1039/b717556f
The dependence of the tautomeric equilibria of cyanomonothiocarbonylmalonamides on the substituents and the solvent and the effect of hydrogen bonding on the configuration/conformation of the enols and thioenols were investigated.
Solar one-way photoisomerisation of 5,8-cyclo-2-deoxyadenosine
Liliana B. Jimenez, Susana Encinas, Chryssostomos Chatgilialoglu and Miguel A. Miranda,
Org. Biomol. Chem., 2008, 6, 1083
DOI: 10.1039/b718222h
Under sunlight irradiation (5S)-5,8-cyclo-2-deoxyadenosine 2 photoisomerises to the (5R) isomer 1, which is the more easily repaired damage when these cyclopurine lesions are formed in DNA.
Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures
Karin Mannerstedt, Eva Segerstedt, Johan Olsson and Stefan Oscarson,
Org. Biomol. Chem., 2008, 6, 1087
DOI: 10.1039/b717564g
Biotin conjugates of a conserved tetrasaccharide structure from the LPS inner core of Haemophilus influenzae containing three heptose residues and a phosphoethanolamine moiety have been synthesised.
Steric effects of polar substituents evaluated in terms of energy by means of isodesmic reactions
Stanislav Böhm and Otto Exner,
Org. Biomol. Chem., 2008, 6, 1092
DOI: 10.1039/b717913h
Steric effects of substituents can be measured quantitatively by the reaction energy of isodesmic reactions, in which a sterically crowded disubstituted compound is produced from two mono derivatives. In the case of charged or strongly polar groups, this steric effect is not pure but includes some effect of induced charges.
Antioxidant activity of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate, from Petiveria alliacea L.
Youji Okada, Kaoru Tanaka, Eisuke Sato and Haruo Okajima,
Org. Biomol. Chem., 2008, 6, 1097
DOI: 10.1039/b715727d
BPT shows effective inhibition of cumene and methyl linoleate oxidation. In addition, one molecule of BPT can scavenge two molecules of peroxyl radicals.
Do garlic-derived allyl sulfides scavenge peroxyl radicals?
Riccardo Amorati and Gian Franco Pedulli,
Org. Biomol. Chem., 2008, 6, 1103
DOI: 10.1039/b719348c
On H-atom abstraction, allyl sulfides give alkyl radicals that react with O2 to form peroxyl radicals, therefore they cannot be considered chain-breaking antioxidants.
N-Heterocyclic carbene catalysed 
-lactam synthesis
Nicolas Duguet, Craig D. Campbell, Alexandra M. Z. Slawin and Andrew D. Smith,
Org. Biomol. Chem., 2008, 6, 1108
DOI: 10.1039/b800857b Enhanced HTML article available
N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding -lactams; chiral NHCs give -lactams in high e.e. after crystallisation.
Promotion of sugar–lectin recognition through the multiple sugar presentation offered by regioselectively addressable functionalized templates (RAFT): a QCM-D and SPR study
Marie Wilczewski, Angéline Van der Heyden, Olivier Renaudet, Pascal Dumy, Liliane Coche-Guérente and Pierre Labbé,
Org. Biomol. Chem., 2008, 6, 1114
DOI: 10.1039/b716214f
The kinetics and thermodynamics of the interaction between the lectin concanavalin A and multi- and monovalent neoglycopeptides based on regioselectively addressable functionalized templates (RAFT) were investigated by nanogravimetry (QCM-D) and surface plasmon resonance (SPR).
Back matter
Org. Biomol. Chem., 2008, 6, 1123
DOI: 10.1039/b802986p
Back cover
Org. Biomol. Chem., 2008, 6, 1127
DOI: 10.1039/b802987n
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