Synthesis and structure determination of FR109615, a new antifungal antibiotic.
The structure of FR109615, a new antifungal antibiotic, was determined to be (1R,2S)-2-aminocyclopentane-1-carboxylic acid ((-)-cis-2-ACPC: 8a) by X-ray analysis. (-)-cis-2-ACPC (8a) was also synthesized via optical resolution of 3a and 3b derived from (+/-)-cis-2-ACPC hydrochloride (1). 8a showed potent antifungal activity, while its antipode (+)-cis-2-ACPC (8b) had no activity.
Kawabata
K
K
New Drug Research Laboratories, Fujisawa Pharmaceutical Co., Ltd., Osaka, Japan.
Inamoto
Y
Y
Sakane
K
K
Iwamoto
T
T
Hashimoto
S
S
D000935:Antifungal Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D002175:Candida / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003515:Cycloleucine / Q000032:analysis / Q000138:chemical synthesis / Q000494:pharmacology / Q000031:analogs & derivatives; D007536:Isomerism; D008968:Molecular Conformation; D015394:Molecular Structure; D013302:Streptomyces; D014961:X-Ray Diffraction
D000935:Antifungal Agents; D003515:Cycloleucine; C065594:cispentacin