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Total Synthesis of the Antiviral Peptide Antibiotic Feglymycin
Author(s) -
Dettner Frank,
Hänchen Anne,
Schols Dominique,
Toti Luigi,
Nußer Antje,
Süssmuth Roderich D.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804130
Subject(s) - epimer , peptide , enantiomer , chemistry , stereochemistry , stereoselectivity , staphylococcus aureus , combinatorial chemistry , glycine , peptide synthesis , antibiotics , stereoisomerism , antibacterial agent , aryl , molecule , biology , biochemistry , amino acid , bacteria , organic chemistry , catalysis , alkyl , genetics
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.