Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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A coumarin based gold(I)-alkynyl complex: a new class of supramolecular hydrogelators

10 February, 2015 - 11:54

Org. Biomol. Chem., 2015, 13,2026-2033
DOI: 10.1039/C4OB02077D, PaperArtur J. Moro, Bertrand Rome, Elisabet Aguilo, Julia Arcau, Rakesh Puttreddy, Kari Rissanen, Joao Carlos Lima, Laura Rodriguez
A phosphine-gold(I)-alkynyl-coumarin complex, [Au{7-(prop-2-ine-1-yloxy)-1-benzopyran-2-one}(DAPTA)] (1), was synthesized and the formation of long luminescent fibers in solution was characterized via fluorescence microscopy and dynamic light scattering.
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Conformational modulation of peptides using [small beta]-amino benzenesulfonic acid (SAnt)

10 February, 2015 - 11:54

Org. Biomol. Chem., 2015, 13,2087-2091
DOI: 10.1039/C4OB02421D, PaperGowri Priya, Amol S. Kotmale, Debamitra Chakravarty, Vedavati G. Puranik, Pattuparambil R. Rajamohanan, Gangadhar J. Sanjayan
This communication describes the utility of the conformationally restricted aromatic [small beta]-amino acid (2-aminobenzenesulfonic acid, SAnt) for inducing various folding interactions in short peptides.
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Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides

10 February, 2015 - 11:54

Org. Biomol. Chem., 2015, 13,2092-2099
DOI: 10.1039/C4OB02318H, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Mathias Pichler, Johanna Novacek, Raphael Robiette, Vanessa Poscher, Markus Himmelsbach, Uwe Monkowius, Norbert Muller, Mario Waser
Phenylglycinol serves as a powerful chiral auxiliary in ammonium ylide-mediated reactions to obtain chiral epoxides/aziridines with excellent stereoselectivities.
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Synthesis of unsaturated phosphatidylinositol 4-phosphates and the effects of substrate unsaturation on SopB phosphatase activity

10 February, 2015 - 11:54

Org. Biomol. Chem., 2015, 13,2001-2011
DOI: 10.1039/C4OB02258K, PaperSamuel Furse, LokHang Mak, Edward W. Tate, Richard H. Templer, Oscar Ces, Rudiger Woscholski, Piers R. J. Gaffney
Single enantiomers of PI-4-P, with a range of sn-2-fatty acid esters, were prepared efficiently. The effects of the degree of sn-2-unsaturation on the kinetic parameters of SopB were determined.
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Synthesis of allylated quinolines/isoquinolines via palladium-catalyzed cyclization-allylation of azides and allyl methyl carbonate

8 February, 2015 - 11:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02567A, PaperJiang Luo, Zhibao Huo, Jun Fu, Fangming Jin, Yoshinori Yamamoto
A novel and efficient strategy for one-step synthesis of allylated quinolines and isoquinolines via palladium-catalyzed cyclization-allylation of azides and allyl methyl carbonate is developed for the first time.
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Construction of the tricyclic core of steenkrotin-type diterpenoids via intramolecular [3 + 2] cycloaddition

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1643-1646
DOI: 10.1039/C4OB02439G, CommunicationJun Xuan, Saiyong Pan, Yuanbao Zhang, Bin Ye, Hanfeng Ding
A concise and diastereoselective route to the [5-6-7] tricyclic skeleton of steenkrotins was developed based on an intramolecular [3 + 2] cycloaddition.
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Bacterial patterning controlled by light exposure

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1639-1642
DOI: 10.1039/C4OB02483D, CommunicationWillem A. Velema, Jan Pieter van der Berg, Wiktor Szymanski, Arnold J. M. Driessen, Ben L. Feringa
Patterning of multiple bacterial strains in one system is achieved by employing a single photo-activated antibiotic.
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N-Phosphonyl/phosphinyl imines and group-assisted purification (GAP) chemistry/technology

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1600-1617
DOI: 10.1039/C4OB02254H, Review ArticleGuanghui An, Cole Seifert, Guigen Li
Group-assisted purification (GAP) chemistry, which can provide various chiral amines and other functionalities without the use of column chromatography or recrystallization; products are consistently obtained with excellent stereocontrol.
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Chemoenzymatic flow cascade for the synthesis of protected mandelonitrile derivatives

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1634-1638
DOI: 10.1039/C4OB02128B, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Marielle M. E. Delville, Kaspar Koch, Jan C. M. van Hest, Floris P. J. T. Rutjes
Integrated two-step chemoenzymatic continuous flow process for the synthesis of protected cyanohydrins from aldehydes.
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Studies on the diastereoselective oxidation of 1-thio-[small beta]-D-glucopyranosides: synthesis of the usually less favoured RS sulfoxide as a single diastereoisomer

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1904-1914
DOI: 10.1039/C4OB02030H, PaperJuan Francisco Moya-Lopez, Eleonora Elhalem, Rocio Recio, Eleuterio Alvarez, Inmaculada Fernandez, Noureddine Khiar
The exo-anomeric effect paves the way for the synthesis of the usually less favored RS-[small beta]-sulfinyl glycoside as a single diastereoisomer.
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Differentiation of small alkane and alkyl halide constitutional isomers via encapsulation

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1869-1877
DOI: 10.1039/C4OB02357A, PaperMatthew R. Sullivan, Bruce C. Gibb
Previously we have demonstrated that host 1 is capable of hydrocarbon gas separation by selective sequestration of butane from a mixture with propane in the headspace above a solution of the host (C. L. D. Gibb, B. C. Gibb, J. Am. Chem. Soc., 2006, 128, 16498-16499).
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E. coli cells expressing the Baeyer-Villiger monooxygenase 'MO14' (ro03437) from Rhodococcus jostii RHA1 catalyse the gram-scale resolution of a bicyclic ketone in a fermentor

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1897-1903
DOI: 10.1039/C4OB01441C, PaperBenjamin D. Summers, Muhiadin Omar, Thomas O. Ronson, Jared Cartwright, Michael Lloyd, Gideon Grogan
(1S,5R)-2-Oxalactone of >99% ee and (1S,5R)-ketone of 96% ee are produced after approximately 14 h at a temperature of 16 [degree]C.
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Cyclopeptides containing the DEKS motif as conformationally restricted collagen telopeptide analogues: synthesis and conformational analysis

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1878-1896
DOI: 10.1039/C4OB02348J, PaperRobert Wodtke, Gloria Ruiz-Gomez, Manuela Kuchar, M. Teresa Pisabarro, Pavlina Novotna, Marie Urbanova, Jorg Steinbach, Jens Pietzsch, Reik Loser
The conformational stabilisation of the DEKS motif at the [small alpha]1(I) collagen N-telopeptide within a cyclic hexapeptide together with its conformational analysis is described. This sequence is critical for lysyl oxidase-mediated collagen crosslinking, a process which is deregulated during tumour progression.
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Fixation of sulfur dioxide into small molecules

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1592-1599
DOI: 10.1039/C4OB02139H, Review ArticleGang Liu, Congbin Fan, Jie Wu
Recent advances in the insertion of sulfur dioxide under transition metal catalysis or metal-free conditions via a radical process are presented.
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N-heterocyclic carbene-catalyzed [4 + 2] cyclization of 2-bromo-2-enal with 3-alkylenyloxindoles: efficient assembly of spirocarbocyclic oxindole

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1829-1835
DOI: 10.1039/C4OB01706D, PaperYuanwei Xie, Yonglei Que, Tuanjie Li, Ling Zhu, Chenxia Yu, Changsheng Yao
A NHC-catalyzed [4 + 2] cyclization of 2-bromo-2-enal bearing [gamma]-H with 3-alkylenyloxindoles under mild reaction conditions gives spirocarbocyclic oxindoles containing one quaternary carbon with high diastereoselectivies.
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Phosphate binding by a novel Zn(II) complex featuring a trans-1,2-diaminocyclohexane ligand. Effective anion recognition in water

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1860-1868
DOI: 10.1039/C4OB02321H, PaperOscar Francesconi, Matteo Gentili, Francesco Bartoli, Andrea Bencini, Luca Conti, Claudia Giorgi, Stefano Roelens
Excellent affinities and selectivities toward triphosphates are achieved through an adaptive ditopic receptor featuring a metal ion and a macrocyclic polyammonium cation binding sites, concertedly bridging phosphate anions.
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Amphiphilic benzothiadiazole-triphenylamine-based aggregates that emit red light in water

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1818-1828
DOI: 10.1039/C4OB02181A, PaperTsutomu Ishi-i, Ikumi Kitahara, Shimpei Yamada, Yusuke Sanada, Kazuo Sakurai, Asami Tanaka, Naoya Hasebe, Toshitada Yoshihara, Seiji Tobita
An amphiphilic donor-acceptor dye can provide red light emission in water in an aggregate state.
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Studies towards the synthesis of bielschowskysin. Construction of the highly functionalized bicyclo[3.2.0]heptane segment

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1846-1859
DOI: 10.1039/C4OB02182G, PaperAnupam Jana, Sujit Mondal, Subrata Ghosh
A stereocontrolled approach for the construction of a highly functionalized bicyclo[3.2.0]heptane derivative embodying the bridged lactone present in the diterpene bielschowskysin is reported.
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Ambient temperature synthesis of [small beta],[small beta][prime or minute]-fused nickel(II) pyrrolo[1,2-a]pyrazinoporphyrins via a DBSA-catalyzed Pictet-Spengler approach

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1836-1845
DOI: 10.1039/C4OB02370F, PaperDileep Kumar Singh, Mahendra Nath
Synthesis of novel [small beta],[small beta][prime or minute]-fused nickel(II) pyrrolo[1,2-a]pyrazinoporphyrins is accomplished for the first time at ambient temperature via a DBSA-catalyzed Pictet-Spengler approach.
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An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations

4 February, 2015 - 10:17

Org. Biomol. Chem., 2015, 13,1807-1817
DOI: 10.1039/C4OB02526A, PaperEdward Richmond, Kenneth B. Ling, Nicolas Duguet, Lois B. Manton, Nihan Celebi-Olcum, Yu-Hong Lam, Sezen Alsancak, Alexandra M. Z. Slawin, K. N. Houk, Andrew D. Smith
The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates 3-alkyl-3-aryloxindoles in good yields and excellent enantioselectivities.
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