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Issue 14 of OBC
02 July 2009
Read more about the cutting edge chemistry featured in the latest issue of OBC
Call for papers: Enabling Technologies for Organic Synthesis
23 June 2009
OBC is delighted to announce a high-profile web theme issue on Enabling Technologies for Organic Synthesis
Highest ever impact factor for OBC
22 June 2009
Newly released ISI citation data show that OBC's Impact Factor has risen by over 12%
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Contents list for Organic & Biomolecular Chemistry, issue 14, 2009
Front cover
Org. Biomol. Chem., 2009, 7, 2821
DOI: 10.1039/b911916g
Inside front cover
Org. Biomol. Chem., 2009, 7, 2822
DOI: 10.1039/b911917p
Contents and Chemical Science
Org. Biomol. Chem., 2009, 7, 2823
DOI: 10.1039/b911919c
Emerging Area
Enantioselective metal-catalyzed activation of strained rings
Tobias Seiser and Nicolai Cramer,
Org. Biomol. Chem., 2009, 7, 2835
DOI: 10.1039/b904405a
Activation of otherwise inert bonds has significant potential in the design of efficient and synthetically useful transformations. This article describes recent developments in the field of enantioselective activations of strained rings.
Perspective
Recent highlights in the synthesis of highly functionalized pyrimidines
Marco Radi, Silvia Schenone and Maurizio Botta,
Org. Biomol. Chem., 2009, 7, 2841
DOI: 10.1039/b906445a
The pyrimidine scaffold represents an important pharmacophore and is present in many pharmacologically active compounds. This perspective article will briefly outline the most interesting approaches recently reported for the synthesis of highly functionalized pyrimidines.
Communications
Efficient syntheses of phosphonylated isochromenes by regioselective 6-endo-dig addition to carbon-carbon triple bond catalyzed by Pd(OAc)2
Fei Wang, Zhiwei Miao and Ruyu Chen,
Org. Biomol. Chem., 2009, 7, 2848
DOI: 10.1039/b908313h
Palladium(II)-catalyzed cycloisomerization of [(2-alkynylphenyl)hydroxymethyl]phosphonates 6 provides an efficient route to phosphonylated isochromenes 7 in THF at room temperature and the reaction proceeded in a regioselective manner leading to the 6-endo-dig products 7 in moderate to excellent yields.
Size-dependent cation transport by cyclic 
-peptoid ion carriers
Chiara De Cola, Sabina Licen, Daniela Comegna, Emiddio Cafaro, Giuseppe Bifulco, Irene Izzo, Paolo Tecilla and Francesco De Riccardis,
Org. Biomol. Chem., 2009, 7, 2851
DOI: 10.1039/b905665c
The synthesis, conformational features, binding to alkali metal ions and membrane transport of new lipophilic cyclic N-benzyloxyethyl -peptoids are disclosed.
Papers
Porphyrin-linked nitroimidazole antibiotics targeting Porphyromonas gingivalis
Benjamin C.-M. Yap, Grace L. Simpkins, Charles A. Collyer, Neil Hunter and Maxwell J. Crossley,
Org. Biomol. Chem., 2009, 7, 2855
DOI: 10.1039/b904340c
Rational design based on active site for porphyrin recognition and synthesis of porphyrin-linked nitroimidazole antibiotics as alternatives to currently used broad-spectrum nitroimidazole antibiotics. These exhibit superior potency and selectivity towards a key pathogen of periodontal disease.
Exclusive platination of loop adenines in the human telomeric G-quadruplex
Hélène Bertrand, Sophie Bombard, David Monchaud, Eric Talbot, Aurore Guédin, Jean-Louis Mergny, Renate Grünert, Patrick J. Bednarski and Marie-Paule Teulade-Fichou,
Org. Biomol. Chem., 2009, 7, 2864
DOI: 10.1039/b904599f
Exclusive platination of adenines located in the loops of the human telomeric G-quadruplex is observed using Pt(II)-terpyridine derivatives. This single-site platination evidences the involvement of the loop residues in small molecule accommodation by G-quadruplex DNA.
Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: synthesis and bioevaluation of -helical anti-HIV peptide analogues
Shinya Oishi, Hirotaka Kamitani, Yasuyo Kodera, Kentaro Watanabe, Kazuya Kobayashi, Tetsuo Narumi, Kenji Tomita, Hiroaki Ohno, Takeshi Naito, Eiichi Kodama, Masao Matsuoka and Nobutaka Fujii,
Org. Biomol. Chem., 2009, 7, 2872
DOI: 10.1039/b907983a
The effect of hydrogen bonds in anti-HIV peptides was evaluated using planar peptide bond surrogates.
Dynamic polythioesters via ring-opening polymerization of 1,4-thiazine-2,5-diones
Yasuyuki Ura, Mohammad Al-Sayah, Javier Montenegro, John M. Beierle, Luke J. Leman and M. Reza Ghadiri,
Org. Biomol. Chem., 2009, 7, 2878
DOI: 10.1039/b903612a
Novel thioester-based polymers that undergo dynamic constitutional exchange under mild conditions can be generated via reversible ring-opening transthioesterification of several 1,4-thiazine-2,5-dione monomers.
Stabilizing unusual conformations in small peptides and glucopeptides using a hydroxylated cyclobutane amino acid
Alberto Fernández-Tejada, Francisco Corzana, Jesús H. Busto, Alberto Avenoza and Jesús M. Peregrina,
Org. Biomol. Chem., 2009, 7, 2885
DOI: 10.1039/b907091p
The first example of a glycopeptide containing a carbohydrate moiety linked to an underlying non-natural amino acid residue is reported. In contrast to natural derivatives, the carbohydrate moiety appears to stabilize extended conformations of the peptide due to the existence of inter-residue hydrogen bonds.
O-Acyl isopeptide method: efficient synthesis of isopeptide segment and application to racemization-free segment condensation
Taku Yoshiya, Hiroyuki Kawashima, Youhei Sohma, Tooru Kimura and Yoshiaki Kiso,
Org. Biomol. Chem., 2009, 7, 2894
DOI: 10.1039/b903624e
We report an O-acyl isopeptide method-based racemization-free segment condensation reaction. The sequential condensation reactions using isopeptide segments containing C-terminal Ser/Thr residues were successfully completed without epimerization.
Peptide-nucleic acids (PNAs) with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone (PPT) as a universal base: their synthesis and binding affinity for oligodeoxyribonucleotides
Taisuke Hirano, Kenji Kuroda, Masanori Kataoka and Yoshihiro Hayakawa,
Org. Biomol. Chem., 2009, 7, 2905
DOI: 10.1039/b821193k
Peptide-nucleic acids including PPT as a nucleobase were synthesized, and their binding affinity for the complementary oligodeoxyribonucleotides was investigated.
Stereocontrolled synthesis of orthogonally protected 2-substituted 4-aminopiperidines
Ramón Badorrey, Elsa Portaña, María D. Díaz-de-Villegas and José A. Gálvez,
Org. Biomol. Chem., 2009, 7, 2912
DOI: 10.1039/b904948g
A rapid entry to 2-substituted 4-aminopiperidines starting from the carbohydrate chiral pool is reported. In the described protocol the stereoselectivity of the procedure is fully guaranteed and controlled.
Concurrent primary and secondary deuterium kinetic isotope effects in anilinolysis of O-aryl methyl phosphonochloridothioates
Md. Ehtesham Ul Hoque, Arun Kanti Guha, Chan Kyung Kim, Bon-Su Lee and Hai Whang Lee,
Org. Biomol. Chem., 2009, 7, 2919
DOI: 10.1039/b903148k
The title reactions, in MeCN at 55.0 °C, exhibit discrete non-linear free energy correlations. Deuterium kinetic isotope effects involving deuterated anilines (XC6H4ND2) are primary (kH/kD = 1.03–1.30) for stronger nucleophiles whereas they are extremely large secondary inverse (kH/kD = 0.367–0.567) for weaker nucleophiles.
Synergy between chemo- and bio-catalysts in multi-step transformations
Aldo Caiazzo, Paula M. L. Garcia, Ron Wever, Jan C. M. van Hest, Alan E. Rowan and Joost N. H. Reek,
Org. Biomol. Chem., 2009, 7, 2926
DOI: 10.1039/b901592b
The successful combination of a lipase catalyzed amidation with palladium catalyzed coupling reactions was achieved on the same substrate. An unexpected synergistic effect between the chemo- and bio-catalysts was observed.
A simple method for C-6 modification of guanine nucleosides
Mahesh K. Lakshman and Josh Frank,
Org. Biomol. Chem., 2009, 7, 2933
DOI: 10.1039/b905298d
Chemical modification at the C-6 position of guanine nucleosides can be readily accomplished through SNAr reactions of the easily synthesized O6-(benzotriazol-1-yl) nucleoside derivatives with amine, alcohol, thiol and phenol nucleophiles.
Self-cleavable chemiluminescent probes suitable for protease sensing
Jean-Alexandre Richard, Ludovic Jean, Caroline Schenkels, Marc Massonneau, Anthony Romieu and Pierre-Yves Renard,
Org. Biomol. Chem., 2009, 7, 2941
DOI: 10.1039/b905725k
Reactive chemical adaptors were used to design the first chemiluminescent probes suitable for detecting protease activities. The PABA traceless linker proved to efficiently release the light-emitting phenolic 1,2-dioxetane moiety under physiological conditions through an enzyme-initiated domino reaction.
Kinetics and mechanism of thermal decomposition of kynurenines and biomolecular conjugates: Ramifications for the modification of mammalian eye lens proteins
Lyudmila V. Kopylova, Olga A. Snytnikova, Elena I. Chernyak, Sergey V. Morozov, Malcolm D. E. Forbes and Yuri P. Tsentalovich,
Org. Biomol. Chem., 2009, 7, 2958
DOI: 10.1039/b903196k
Kynurenines are UV-filter compounds found in mammalian eye lenses, whose degradation leads to age-related cataract disease. The mechanism of one such pathway, deamination, proceeds by generalized base catalysis.
A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds
Shao-Feng Wu, Xiao Zheng, Yuan-Ping Ruan and Pei-Qiang Huang,
Org. Biomol. Chem., 2009, 7, 2967
DOI: 10.1039/b906224f
A new approach to trans-(3S)-hydroxyprolinol derivatives was developed based on the SmI2-mediated reductive coupling of the (S)-malic acid derived chiral nitrone 10 with carbonyl compounds.
Complementary chemoenzymatic routes to both enantiomers of febrifugine
Marloes A. Wijdeven, Rutger J. F. van den Berg, Roel Wijtmans, Peter N. M. Botman, Richard H. Blaauw, Hans E. Schoemaker, Floris L. van Delft and Floris P. J. T. Rutjes,
Org. Biomol. Chem., 2009, 7, 2976
DOI: 10.1039/b901670h
Two different complementary chemoenzymatic strategies to both enantiomers of febrifugine have been developed.
A concise approach to the core structures of pinnaic acid and halichlorine
Sung-Hyun Yang, G. R. Clark and Vittorio Caprio,
Org. Biomol. Chem., 2009, 7, 2981
DOI: 10.1039/b903904j
A highly concise synthesis of the azaspiro[4.5]decane core structures of the marine anti-inflammatory alkaloids pinnaic acid 25 and halichlorine 6is described from key spirocyclic nitrone 4. This synthesis is highly amenable to scale up and to the preparation of an array of structural analogues.
Back cover
Org. Biomol. Chem., 2009, 7, 2991
DOI: 10.1039/b911920p
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