Org. and Biomol. Chem.

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Improved synthesis of the super antioxidant, ergothioneine and its biosynthetic pathway intermediates.

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02023E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Anwar Jardine, Peguy Lutete Khonde
Ergothioneine along with mycothiol, are low molecular mass redox protective thiols present in Actinomycetes, in particular mycobacteria. We report the improved chemical synthesis of ergothioneine (ESH) and biosynthetic pathway intermediates...
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Synthesis and Antifungal Activity of 1,2,3-Triazole Phenylhydrazone Derivatives

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01758G, PaperZhicheng Dai, Yongfei Chen, Mao Zhang, Shengkun Li, Tingting Yang, Li Shen, Jianxin Wang, Shao-Song Qian, Hai-Liang Zhu, Yonghao Ye
A series of 1,2,3-triazole phenylhydrazone were designed and synthesized as antifungal agents. Their structures were determined based on 1H-NMR spectroscopy, MS, elemental analysis and X-ray single-crystal diffraction. The antifungal activities...
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Chiral recognition with a benzofuran receptor which mimics an oxyanion hole

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01954G, PaperAngel L. Fuentes de Arriba, Angel Gomez Herrero, Omayra Hernandez Rubio, Laura Marcos Monleon, Luis Simon, Victoria Alcazar, Francisca Sanz, Joaquin Rodriguez Moran
A new chiral benzofuran receptor has been synthesized and its properties in the association of amino acid derivatives have been studied. X-ray structures were obtained and these corroborate the presence...
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Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01860E, PaperPhilipp Ensslen, Yannic Fritz, Hans-Achim Wagenknecht
Ethynyl pyrene and ethynyl nile red as modifications at the 5-position of 2'-deoxuridines self-assemble non-covalently and specifically along oligo-2'-deoxyadenosines as templates. Oligo-2'-deoxyadenosines of the lengths (dA)10 - (dA)20 are able...
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Efficient Merging of Copper and Photoredox Catalysis for the Asymmetric Cross-Dehydrogenative-Coupling of Alkynes and Tetrahydroisoquinolines

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02138J, PaperInna Perepichka, Soumen Kundu, Zoe Hearne, Chao-Jun Li
A highly efficient catalytic asymmetric alkynylation of prochiral CH2 groups in tetrahydroisoquinoline was developed using copper catalyzed cross-dehydrogenative-coupling of sp3 and sp C-H bonds with the assistance of a photocatalyst...
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Correction: Non-isoprenoid polyene natural products - structures and synthetic strategies

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, 12,9029-9031
DOI: 10.1039/C4OB90153C, CorrectionKatrina S. Madden, Fathia A. Mosa, Andrew Whiting
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Synthesis of highly functionalized C60 fullerene derivatives and their applications in material and life sciences

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01663G, Review ArticleWeibo Yan, Stefan M. Seifermann, Philippe Pierrat, Stefan Brase
Highly functionalized fullerenes can be efficiently constructed by various techniques.
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Correction: Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

28 October, 2014 - 10:17
Org. Biomol. Chem., 2014, 12,9028-9028
DOI: 10.1039/C4OB90144D, CorrectionRosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Michael Shipman, Saverio Florio, Renzo Luisi
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Organocatalytic Michael addition-lactonisation of carboxylic acids using [small alpha],[small beta]-unsaturated trichloromethyl ketones as [small alpha],[small beta]-unsaturated ester equivalents

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,9016-9027
DOI: 10.1039/C4OB01788A, PaperLouis C. Morrill, Daniel G. Stark, James E. Taylor, Siobhan R. Smith, James A. Squires, Agathe C. A. D'Hollander, Carmen Simal, Peter Shapland, Timothy J. C. O'Riordan, Andrew D. Smith
Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and [small alpha],[small beta]-unsaturated trichloromethyl ketones.
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Templated DNA ligation with thiol chemistry

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8823-8827
DOI: 10.1039/C4OB01552E, CommunicationDadong Li, Xiaojian Wang, Fubo Shi, Ruojie Sha, Nadrian C. Seeman, James W. Canary
Templated DNA ligation reactions are useful in a variety of contexts and have drawn much attention recently. Herein we describe two different DNA-templated ligation systems based on thiols and thiol-mediated chemistry. One system follows the principle of native chemical ligation reaction, and the other utilizes a thiol-disulfide exchange reaction.
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A short designed semi-aromatic organic nanotube - synthesis, chiroptical characterization, and host properties

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8930-8941
DOI: 10.1039/C4OB01683A, PaperTorbjorn Wixe, Niels Johan Christensen, Sven Lidin, Peter Fristrup, Kenneth Warnmark
A short helical nanotube having its aromatic system perpendicular to its axis of propagation was synthesized and its properties were studied.
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Transition metal ion induced hydrogelation by amino-terpyridine ligands

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8836-8839
DOI: 10.1039/C4OB01867B, CommunicationSandip Bhowmik, Biswa Nath Ghosh, Kari Rissanen
Hydrogelation behavior of a new class of terpyridine based metallogelators are explored. The gelation and the gel morphology was found to be critically dependent on divalent metal ions, anions and on subtle structural changes on the gelator molecule.
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Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01649A, PerspectiveMadhu Sudan Manna, Santanu Mukherjee
Asymmetric desymmetrization represents an excellent strategy for obtaining highly functionalized chiral building blocks. However, the application of this strategy for the synthesis of cyclopentane derivatives remained limited, when compared to cyclohexanes. Here, we give an overview of asymmetric desymmetrization reactions leading to enantioenriched cyclopentanes.
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Protein backbone engineering as a strategy to advance foldamers toward the frontier of protein-like tertiary structure

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8796-8802
DOI: 10.1039/C4OB01769B, PerspectiveZachary E. Reinert, W. Seth Horne
This Perspective surveys work on protein backbone engineering and its recent application to design heterogeneous backbones that adopt complex tertiary folds.
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Pseudo-cyclic structures of mono- and di-azaderivatives of malondialdehydes. Synthesis and conformational disentanglement by computational analyses

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8997-9010
DOI: 10.1039/C4OB01507J, PaperMaria P. Romero-Fernandez, Martin Avalos, Reyes Babiano, Pedro Cintas, Jose L. Jimenez, Mark E. Light, Juan C. Palacios
Aminoacroleins and vinamidines are structures featuring H-bonding and complex conformational and tautomeric equilibria, which have been dissected by computation.
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Synthesis of functionalized fulvenes: [3 + 2] annulation of ethyl [small alpha]-chlorocyclopropaneformates with 1,3-dicarbonyl compounds

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8828-8831
DOI: 10.1039/C4OB01973C, CommunicationYuequan Zhu, Min Zhang, Hongling Yuan, Yuefa Gong
An efficient method is reported to produce acidic multi-substituted fulvenes at high yields (up to 94%) through the base-promoted [3 + 2] annulation reaction of ethyl [small alpha]-chlorocyclopropaneformates with 1,3-dicarbonyl compounds.
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Approaches to design non-covalent inhibitors for human granzyme B (hGrB)

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8952-8965
DOI: 10.1039/C4OB01874E, PaperMi-Sun Kim, Lauriane A. Buisson, Dean A. Heathcote, Haipeng Hu, D. Christopher Braddock, Anthony G. M. Barrett, Philip G. Ashton-Rickardt, James P. Snyder
A structure-based design campaign for non-covalent small molecule inhibitors of hGrB was carried out by virtual screening employing three constraints and probe site-mapping with FTMAP to identify ligand "hot spots".
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Chemical and biological evaluation of unusual sugars, [small alpha]-aculosides, as novel Michael acceptors

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8832-8835
DOI: 10.1039/C4OB01877J, CommunicationHiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, Daisuke Takahashi, Kazunobu Toshima
Unusual sugars, [small alpha]-aculosides, were found to be novel and selective Michael acceptors to a thiol function of cysteine residues of proteins in living cells.
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A straightforward modification in the thrombin binding aptamer improving the stability, affinity to thrombin and nuclease resistance

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8840-8843
DOI: 10.1039/C4OB01475H, CommunicationVeronica Esposito, Maria Scuotto, Antonella Capuozzo, Rita Santamaria, Michela Varra, Luciano Mayol, Antonella Virgilio, Aldo Galeone
Introduction of inversion of polarity sites at the 5[prime or minute]- and/or 3[prime or minute]-end in the thrombin binding aptamer is a simple modification able to improve, at the same time, thermal stability, affinity to thrombin and nuclease resistance.
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The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against the pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8911-8918
DOI: 10.1039/C4OB01347F, PaperLingling Feng, Junbo He, Haifeng He, Lulu Zhao, Lingfu Deng, Li Zhang, Lin Zhang, Yanliang Ren, Jian Wan, Hongwu He
Optimal binding mode for the novel potent inhibitor 4j against PDHc-E1 from E. coli.
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