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New Editor announcement
26 January 2010
We are pleased to announce Richard Kelly as the new Editor of Organic & Biomolecular Chemistry and Natural Product Reports.
OBC Lecture Award winner 2010 announced
25 January 2010
The 2010 OBC Lecture Award has been won by Professor Michael Burkart, at the University of California - San Diego, in the US.
NPR Lecture Award winner 2010 announced
25 January 2010
The 2010 Natural Product Reports Lecture Award has been won by Professor Christopher Walsh, at Harvard Medical School, in the US.
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Contents list for Organic & Biomolecular Chemistry, issue 4, 2010
Front cover
Org. Biomol. Chem., 2010, 8, 717
DOI: 10.1039/C001242B
Inside front cover
Org. Biomol. Chem., 2010, 8, 718
DOI: 10.1039/C001243M
Contents
Org. Biomol. Chem., 2010, 8, 719
DOI: 10.1039/C001244K
Emerging Area
Getting a chemical handle on protein post-translational modification
William P. Heal and Edward W. Tate,
Org. Biomol. Chem., 2010, 8, 731
DOI: 10.1039/b917894e
Chemical proteomics is a powerful technology for the study of post- and co-translational modification of proteins. Here, we review techniques that combine protein-modifying enzymes with bioorthogonal chemoselective elaboration to enable new advances in our understanding of protein modification.
Perspective
Steroid hormones controlling the life cycle of the nematode Caenorhabditis elegans: stereoselective synthesis and biology
René Martin, Eugeni V. Entchev, Teymuras V. Kurzchalia and Hans-Joachim Knölker,
Org. Biomol. Chem., 2010, 8, 739
DOI: 10.1039/b918488k
Cholesterol-derived hormones, the dafachronic acids, play a major role in controlling the life cycle and initiating dauer larva formation of the nematode Caenorhabditis elegans. This Perspective describes recent progress in the synthesis of these steroid hormones and their biological function.
Communications
Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks
Kerrie A. B. Austin, Jon D. Elsworth, Martin G. Banwell and Anthony C. Willis,
Org. Biomol. Chem., 2010, 8, 751
DOI: 10.1039/b921600f
The chemoenzymatically derived triene undergoes a facially-selective IMDA reaction to give an adduct incorporating the carbocyclic framework of the sesquiterpene (-)-khusiol.
Enantioselective construction of lactone[2,3-b]piperidine skeletons via organocatalytic tandem reactions
Zhao-Quan He, Bo Han, Rui Li, Li Wu and Ying-Chun Chen,
Org. Biomol. Chem., 2010, 8, 755
DOI: 10.1039/b922053d
A highly enantioselective construction of 
- and 
-lactone[2,3-b]piperidine skeletons was accomplished by tandem aza-Diels–Alder reaction–hemiacetal formation–oxidation from N-Tos-1-aza-1,3-butadienes and aliphatic dialdehydes.
Enantioselective desymmetrizing palladium catalyzed carbonylation reactions: the catalytic asymmetric synthesis of quaternary carbon center containing 1,3-dienes
Simon J. Byrne, Anthony J. Fletcher, Paul Hebeisen and Michael C. Willis,
Org. Biomol. Chem., 2010, 8, 758
DOI: 10.1039/b923186b
A desymmetrization protocol has been used to develop a palladium catalyzed enantioselective carbonylation process. Achiral cyclic bis-alkenyltriflates are converted to their corresponding monoester derivatives with selectivities of up to 96% ee.
A novel pseudo four component reaction involving homoenolate for the synthesis of -aminobutyric acid (GABA) derivatives
Vijay Nair, Vimal Varghese, Beneesh P. Babu, C. R. Sinu and Eringathodi Suresh,
Org. Biomol. Chem., 2010, 8, 761
DOI: 10.1039/b922981g
Homoenolate generated from 
,
-unsaturated aldehydes by NHC catalysis underwent facile addition to conjugated sulfonimines and subsequent methanolysis to afford protected GABA derivatives stereoselectively and in high yields, thus constituting a novel pseudo four component reaction.
Papers
Solid state stabilisation of the orally delivered drugs atenolol, glibenclamide, memantine and paracetamol through their complexation with cucurbit[7]uril
Fiona J. McInnes, Nahoum G. Anthony, Alan R. Kennedy and Nial J. Wheate,
Org. Biomol. Chem., 2010, 8, 765
DOI: 10.1039/b918372h
The inclusion of the cardiovascular -blocker drug atenolol, the antidiabetic drug glibenclamide, the Alzheimer's drug memantine and the analgesic paracetamol by cucurbit[7]uril has been studied by NMR, ESI-MS, molecular modelling, fluorescence displacement assays and DSC.
Solvent-induced switching between two supramolecular assemblies of a guanosine–terthiophene conjugate
Silvia Pieraccini, Sara Bonacchi, Stefano Lena, Stefano Masiero, Marco Montalti, Nelsi Zaccheroni and Gian Piero Spada,
Org. Biomol. Chem., 2010, 8, 774
DOI: 10.1039/b920220j
The guanosine–terthiophene conjugate undergoes a pronounced variation of its supramolecular organisation from a guanine-directed to a terthienyl-directed assembly by changing the polarity of the solvent.
Site-selective immobilisation of functional enzymes on to polystyrene nanoparticles
Lu Shin Wong, Krzysztof Okrasa and Jason Micklefield,
Org. Biomol. Chem., 2010, 8, 782
DOI: 10.1039/b916773k
Site-selective covalent immobilisation of ybbR tagged proteins, including functional enzymes, on to nanoparticles derivatised with CoA is achieved in a mild and efficient reaction catalysed by the promiscuous phosphopantetheinyl transferase Sfp.
Helix propensities of conformationally restricted amino acids. Non-natural substitutes for helix breaking proline and helix forming alanine
Miriam Alías, Sara Ayuso-Tejedor, Juan Fernández-Recio, Carlos Cativiela and Javier Sancho,
Org. Biomol. Chem., 2010, 8, 788
DOI: 10.1039/b919671d
Helix propagation parameters of the conformationally restricted amino acids Aib and Ac3c as an aid for helical peptide designing.
Improved enzymatic syntheses of valuable -arylalkyl--amino acid enantiomers
Gábor Tasnádi, Enik
Forró and Ferenc Fülöp,
Org. Biomol. Chem., 2010, 8, 793
DOI: 10.1039/b920731g
The enantioselective (E
200) Burkholderia cepacia-catalysed hydrolyses of -amino esters with H2O (0.5 equiv.) in t-BuOMe or in i-Pr2O at 45 °C are described. The enantiomers were prepared with high enantiomeric excesses (ee >96%) and in good yields (>42%).
Photochemistry of dihydrobiopterin in aqueous solution
Mariana Vignoni, Franco M. Cabrerizo, Carolina Lorente, Catherine Claparols, Esther Oliveros and Andrés H. Thomas,
Org. Biomol. Chem., 2010, 8, 800
DOI: 10.1039/b913095k
Photooxidation of pterins takes place in vivo under pathological conditions. We have investigated the photochemistry of dihydrobiopterin and discuss the mechanisms involved.
The enantioselective total synthesis of nemotin
Ya-Jun Jian and Yikang Wu,
Org. Biomol. Chem., 2010, 8, 811
DOI: 10.1039/b923123d
The gross structure of nemotin was established in the 1950s, but the stereochemistry remains unknown to date. Now, with the aid of an enantioselective synthesis, the (4S,5aS) configuration among the four possible alternatives is shown to represent the natural product.
On the question of stepwise vs. concerted cleavage of RNA models promoted by a synthetic dinuclear Zn(II) complex in methanol: implementation of a noncleavable phosphonate probe
David R. Edwards, Wing-Yin Tsang, Alexei A. Neverov and R. Stan Brown,
Org. Biomol. Chem., 2010, 8, 822
DOI: 10.1039/b918310h
Zn(II)2 complex ( 4) does not promote the interconversion of isomeric phosphonates ( 6a, 6b), the only products of the reaction being 1,2-propanediol and O-methyl phenylphosphonate.
5-Selenization of salicylic acid derivatives yielded isoform-specific 5-lipoxygenase inhibitors
Sun-Chol Yu, Hartmut Kuhn, Constantin-Gabriel Daniliuc, Igor Ivanov, Peter G. Jones and Wolf-Walther du Mont,
Org. Biomol. Chem., 2010, 8, 828
DOI: 10.1039/b918778b
5-Seleninic acids or anhydrides of salicylic acid amides or esters are promising inhibitors more selective to recombinant human 5-lipoxygenase than to rabbit reticulocyte 12/15-lipoxygenase.
New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: application of peptide coupling agents EDC and HBTU
Vommina V. Sureshbabu, H. S. Lalithamba, N. Narendra and H. P. Hemantha,
Org. Biomol. Chem., 2010, 8, 835
DOI: 10.1039/b920290k
Acid azides have been efficiently prepared from carboxylic acids using peptide coupling agents EDC or HBTU; and the reaction has been extended to the one pot synthesis of ureas and carbamates from carboxylic acids
Ligand-free copper(I)-catalysed intramolecular direct C–H functionalization of azoles
Nekane Barbero, Raul SanMartin and Esther Domínguez,
Org. Biomol. Chem., 2010, 8, 841
DOI: 10.1039/b916549e
The first examples of copper-catalysed intramolecular direct C-arylation of azaheterocycles for the synthesis of complex heterofused compounds is presented, featuring an unprecedented arylation via C–H activation of 9H-purine and 4-azabenzimidazole.
Insight into the mechanism of action of plakortins, simple 1,2-dioxane antimalarials
Orazio Taglialatela-Scafati, Ernesto Fattorusso, Adriana Romano, Fernando Scala, Vincenzo Barone, Paola Cimino, Emiliano Stendardo, Bruno Catalanotti, Marco Persico and Caterina Fattorusso,
Org. Biomol. Chem., 2010, 8, 846
DOI: 10.1039/b918600j
Computational calculations and chemical reactions give insight into the mechanism of the antimalarial action of plakortin and dihydroplakortin, simple 1,2-dioxanes isolated from a marine sponge.
A new model for mapping the peptide backbone: predicting proton chemical shifts in proteins
José Luis Barneto, Martín Avalos, Reyes Babiano, Pedro Cintas, José Luis Jiménez and Juan Carlos Palacios,
Org. Biomol. Chem., 2010, 8, 857
DOI: 10.1039/b921121g
This study provides a methodology to correlate empirical chemical shifts (at the alpha-proton) in proteins with geometrical data (distances and dihedral angles) calculated at the B3PW91/6-31G* level.
MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis: the cycloaddition approach
Maryse Thiverny, Christian Philouze, Pierre Yves Chavant and Véronique Blandin,
Org. Biomol. Chem., 2010, 8, 864
DOI: 10.1039/b918612c
Totally regio- and diastereo-selective 1,3-dipolar cycloaddition reaction of various alkenes with MiPNO, a new chiral cyclic nitrone, provides an expeditious enantioselective access to unusual -hydroxy -amino acids.
Mechanism of general acid–base catalysis in transesterification of an RNA model phosphodiester studied with strongly basic catalysts
David O. Corona-Martínez, Olga Taran and Anatoly K. Yatsimirsky,
Org. Biomol. Chem., 2010, 8, 873
DOI: 10.1039/b920398b
Classical 
bell-shaped
second-order kinetics of general acid–base catalysis in transesterification of an RNA model substrate absent in aqueous buffers is observed in guanidine and amidine buffers in 80% vol aqueous DMSO.
Synthesis of 3-hydroxy-5-alkoxyhomophthalates by domino 
2
:1-coupling/intramolecular aldol condensation
reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with tetraalkoxymethanes
Mathias Lubbe and Peter Langer,
Org. Biomol. Chem., 2010, 8, 881
DOI: 10.1039/b918466j
The first domino 2:1 condensation/intramolecular aldol reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadiene with tetraalkoxymethanes provide a convenient approach to 3-hydroxy-5-alkoxyhomophthalates.
Formation and hydrolysis of amide bonds by lipase A from Candida antarctica; exceptional features
Arto Liljeblad, Pauli Kallio, Marita Vainio, Jarmo Niemi and Liisa T. Kanerva,
Org. Biomol. Chem., 2010, 8, 886
DOI: 10.1039/b920939p
Exceptional lipase: the ability of lipase A from Candida antarctica (CAL-A) to form and hydrolyze amide bonds was studied with 1a–c, 2a–c, 3a and 4a. The possible role of enzyme contaminants in the reactions was studied by fractionation and sequence-based identification of the commercial CAL-A preparation Cat#ICR-112 (Codexis).
Cross-coupling reaction of alcohols for carbon–carbon bond formation using pincer-type NHC/palladium catalysts
Osamu Kose and Susumu Saito,
Org. Biomol. Chem., 2010, 8, 896
DOI: 10.1039/b914618k
A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H2 gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high product alcohol selectivity.
Nucleophilic heterocyclic carbene as a novel catalyst for cyclopropanation of cyano acrylates
Anabha E. Raveendran, Rony Rajan Paul, Eringathodi Suresh and Vijay Nair,
Org. Biomol. Chem., 2010, 8, 901
DOI: 10.1039/b916343c
Nucleophilic heterocyclic carbenes (NHCs) have been used or the first time as catalysts in the cyclopropanation of ethyl cyanocinnamates with phenacyl bromide by Michael-initiated ring-closure (MIRC).
Glucosylthioureidocalix[4]arenes: Synthesis, conformations and gas phase recognition of amino acids
Mika Torvinen, Raisa Neitola, Francesco Sansone, Laura Baldini, Rocco Ungaro, Alessandro Casnati, Pirjo Vainiotalo and Elina Kalenius,
Org. Biomol. Chem., 2010, 8, 906
DOI: 10.1039/b916268b
Conformational properties of glucosylcalixarenes and their selective complexation with amino acids have been clarified in solution and gas-phase.
Evaluation of stereochemically dense morpholine-based scaffolds as proline surrogates in -turn peptides
Filippo Sladojevich, Antonio Guarna and Andrea Trabocchi,
Org. Biomol. Chem., 2010, 8, 916
DOI: 10.1039/b913444a
NMR analysis of stereochemically dense morpholine-based scaffolds as proline surrogates in -turn peptides revealed an adaptive behaviour in generating turn conformations stabilized by intramolecular hydrogen-bonds with no significant loss of the secondary framework.
Back matter
Org. Biomol. Chem., 2010, 8, 925
DOI: 10.1039/C002042G
Back cover
Org. Biomol. Chem., 2010, 8, 927
DOI: 10.1039/C001245A
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