Pneumocandins from Zalerion arboricola. III. Structure elucidation.
Pneumocandin B0 (6) and six related lipopeptides are antifungal and anti-Pneumocystis carinii agents from mutants of Zalerion arboricola, whose structures were determined mainly on the basis of spectroscopic analysis. They belong, along with pneumocandin A0 (L-671,329) previously isolated from these laboratories, to the echinocandin class of antifungal agents. The product from base-catalyzed ring opening involving the hemiaminal position of the dihydroxyornithine residue of B0, has been clearly defined as 6b. Modifications were limited to the 3-hydroxy-4-methylproline, 3,4-dihydroxyhomotyrosine and 4,5-dihydroxyornithine residues of pneumocandin A0.
Hensens
O D
OD
Department of Natural Products Chemistry, Merck Research Laboratories, Rahway, N.J. 07065-0900.
Liesch
J M
JM
Zink
D L
DL
Smith
J L
JL
Wichmann
C F
CF
Schwartz
R E
RE
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry; D002176:Candida albicans / Q000187:drug effects; D003461:Crystallography; D054714:Echinocandins; D009682:Magnetic Resonance Spectroscopy; D003904:Mitosporic Fungi / Q000737:chemistry*; D010455:Peptides; D010456:Peptides, Cyclic / Q000737:chemistry / Q000494:pharmacology; D011010:Pneumocystis / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000998:Antiviral Agents; D054714:Echinocandins; D010455:Peptides; D010456:Peptides, Cyclic; C058995:pneumocandin A(0); C079465:pneumocandin B(0)