Literature DB >> 10480571

Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp. A92-308110. II. Structure elucidation, stereochemistry and physico-chemical properties.

T Fehr1, J Kallen, L Oberer, J J Sanglier, W Schilling.   

Abstract

A novel class of macrolides, the sanglifehrins, was discovered by screening of actinomycete strains with a cyclophilin-binding assay. The chemical structures and absolute stereochemistries of the sanglifehrins A, B, C and D were determined unambiguously by NMR-techniques and by X-ray crystallography of the complex with cyclophilin A. Sanglifehrin A consists of a 22-membered macrocycle containing a tripeptide subunit and features in position 23 a chain of nine carbon atoms bearing a spirocyclic substituent. Sanglifehrins A and B are genuine metabolites whereas sanglifehrins C and D are artefacts.

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Year:  1999        PMID: 10480571     DOI: 10.7164/antibiotics.52.474

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  11 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 2.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

Review 3.  Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Authors:  Abraham J Waldman; Tai L Ng; Peng Wang; Emily P Balskus
Journal:  Chem Rev       Date:  2017-04-04       Impact factor: 60.622

4.  Cyclosporine blocks incorporation of HIV-1 envelope glycoprotein into virions.

Authors:  Elena Sokolskaja; Silvia Olivari; Madeleine Zufferey; Caterina Strambio-De-Castillia; Massimo Pizzato; Jeremy Luban
Journal:  J Virol       Date:  2010-02-24       Impact factor: 5.103

5.  Preclinical characterization of naturally occurring polyketide cyclophilin inhibitors from the sanglifehrin family.

Authors:  Matthew A Gregory; Michael Bobardt; Susan Obeid; Udayan Chatterji; Nigel J Coates; Teresa Foster; Philippe Gallay; Pieter Leyssen; Steven J Moss; Johan Neyts; Mohammad Nur-e-Alam; Jan Paeshuyse; Mahmood Piraee; Dipen Suthar; Tony Warneck; Ming-Qiang Zhang; Barrie Wilkinson
Journal:  Antimicrob Agents Chemother       Date:  2011-03-07       Impact factor: 5.191

Review 6.  Molecular aspects of cyclophilins mediating therapeutic actions of their ligands.

Authors:  Andrzej Galat; Jacqueline Bua
Journal:  Cell Mol Life Sci       Date:  2010-07-04       Impact factor: 9.261

7.  Biosynthesis of piperazic acid via N5-hydroxy-ornithine in Kutzneria spp. 744.

Authors:  Christopher S Neumann; Wei Jiang; John R Heemstra; Erin A Gontang; Roberto Kolter; Christopher T Walsh
Journal:  Chembiochem       Date:  2012-04-20       Impact factor: 3.164

8.  Target cell cyclophilin A modulates human immunodeficiency virus type 1 infectivity.

Authors:  Elena Sokolskaja; David M Sayah; Jeremy Luban
Journal:  J Virol       Date:  2004-12       Impact factor: 5.103

9.  The cyclophilin-binding agent Sanglifehrin A is a dendritic cell chemokine and migration inhibitor.

Authors:  Sabrina N Immecke; Nelli Baal; Jochen Wilhelm; Juliane Bechtel; Angela Knoche; Gregor Bein; Holger Hackstein
Journal:  PLoS One       Date:  2011-03-31       Impact factor: 3.240

10.  Identification and characterization of the biosynthetic gene cluster of polyoxypeptin A, a potent apoptosis inducer.

Authors:  Yanhua Du; Yemin Wang; Tingting Huang; Meifeng Tao; Zixin Deng; Shuangjun Lin
Journal:  BMC Microbiol       Date:  2014-02-08       Impact factor: 3.605

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