Communication

Total Synthesis of the Antiviral Peptide Antibiotic Feglymycin†

  1. Frank Dettner1,
  2. Anne Hänchen1,
  3. Dominique Schols Prof. Dr.2,
  4. Luigi Toti Dr.3,
  5. Antje Nußer3,
  6. Roderich D. Süssmuth Prof. Dr.1

Article first published online: 29 JAN 2009

DOI: 10.1002/anie.200804130

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 10, pages 1856–1861, February 23, 2009

Additional Information

How to Cite

Dettner, F., Hänchen, A., Schols, D., Toti, L., Nußer, A. and Süssmuth, Roderich D. (2009), Total Synthesis of the Antiviral Peptide Antibiotic Feglymycin. Angew. Chem. Int. Ed., 48: 1856–1861. doi: 10.1002/anie.200804130

Author Information

  1. 1

    Technische Universität Berlin, Fakultät II—Institut für Chemie, Strasse des 17. Juni 124, 10623 Berlin (Germany), Fax: (+49) 30-314-24205 http://www2.tu-berlin.de/fb5/Suessmuth/?L=0

  2. 2

    Rega Institute, Laboratory of Virology and Chemotherapy, Minderbroedersstraat 10, 3000 Leuven (Belgium)

  3. 3

    Sanofi-Aventis Deutschland GmbH, R&D CAS Natural Products, Industriepark Hoechst, H811, 65926 Frankfurt am Main (Germany)

  1. †

    DFG grant SU 239/7-1.

Publication History

  1. Issue published online: 17 FEB 2009
  2. Article first published online: 29 JAN 2009
  3. Manuscript Revised: 22 OCT 2008
  4. Manuscript Received: 21 AUG 2008

Funded by

  • DFG. Grant Number: SU 239/7-1

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Keywords:

  • aryl glycines;
  • epimerization;
  • HIV;
  • peptide antibiotics;
  • total synthesis

Abstract

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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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