Azadepsipeptides: synthesis and evaluation of a novel class of peptidomimetics.
A general route to azadepsipeptides, a new class of pseudopeptides, has been established. The methodology was applied to the synthesis of a bis-aza analogue of the antiparasitic cyclooctadepsipeptide PF1022A. Comparison of the X-ray crystal structures of natural PF1022A (8) and the chimeric aza analogue 9 revealed that the introduction of nitrogen in the backbone of PF1022A results in almost complete conservation of the 3D structure with only minor deviations at the new nitrogen positions.
Dyker
H
H
Central Research and Business Group Animal Health, Bayer AG, D-51368 Leverkusen, Germany.
Scherkenbeck
J
J
Gondol
D
D
Goehrt
A
A
Harder
A
A
D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D047630:Depsipeptides; D006188:Haemonchiasis / Q000188:drug therapy / Q000469:parasitology; D006189:Haemonchus; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D012756:Sheep; D014253:Trichostrongylosis / Q000188:drug therapy / Q000469:parasitology; D014254:Trichostrongylus
D000871:Anthelmintics; D047630:Depsipeptides; D007202:Indicators and Reagents; D009842:Oligopeptides; D010456:Peptides, Cyclic; C075544:PF 1022A