Literature DB >> 19180618

Total synthesis of the antiviral peptide antibiotic feglymycin.

Frank Dettner1, Anne Hänchen, Dominique Schols, Luigi Toti, Antje Nusser, Roderich D Süssmuth.   

Abstract

An adaptable approach: The first highly convergent stereoselective synthesis of feglymycin (see structure) and its enantiomer is based on the coupling of repeating peptide fragments. The use of weakly basic conditions throughout the synthesis suppressed the epimerization of sensitive aryl glycine units. Feglymycin has strong anti-HIV activity as well as potent (previously identified as weak) antibacterial activity against Staphylococcus aureus.

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Year:  2009        PMID： 19180618     DOI： 10.1002/anie.200804130

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  4 in total

Review 1.  Advances in MRSA drug discovery: where are we and where do we need to be?

Authors:  Michio Kurosu; Shajila Siricilla; Katsuhiko Mitachi
Journal:  Expert Opin Drug Discov       Date:  2013-07-06       Impact factor: 6.098

2.  Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate.

Authors:  Victoria T Lim; Sergey V Tsukanov; Amanda B Stephens; Jeffrey N Johnston
Journal:  Organic Synth       Date:  2016

3.  Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation.

Authors:  Shinichiro Fuse; Yuto Mifune; Hiroyuki Nakamura; Hiroshi Tanaka
Journal:  Nat Commun       Date:  2016-11-28       Impact factor: 14.919

4.  Synthetic Lugdunin Analogues Reveal Essential Structural Motifs for Antimicrobial Action and Proton Translocation Capability.

Authors:  Nadine A Schilling; Anne Berscheid; Johannes Schumacher; Julian S Saur; Martin C Konnerth; Sebastian N Wirtz; José M Beltrán-Beleña; Alexander Zipperer; Bernhard Krismer; Andreas Peschel; Hubert Kalbacher; Heike Brötz-Oesterhelt; Claudia Steinem; Stephanie Grond
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-27       Impact factor: 15.336
  4 in total

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