Total synthesis of the antiviral peptide antibiotic feglymycin.
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.
Dettner
Frank
F
Technische Universität Berlin, Fakultät II-Institut für Chemie, Strasse des 17. Juni 124, 10623 Berlin, Germany.
Hänchen
Anne
A
Schols
Dominique
D
Toti
Luigi
L
Nusser
Antje
A
Süssmuth
Roderich D
RD
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D020128:Inhibitory Concentration 50; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D010455:Peptides; D011506:Proteins; C120179:feglymycin