Absolute stereochemistry of the strevertenes.
The CD exciton chirality method was applied to determine the absolute stereochemistry of the strevertenes, antifungal pentaene macrolides produced by Streptoverticillium sp. LL-30F848. The CD difference spectrum of strevertene A methyl ester 15-dimethylaminobenzoate showed a positive couplet between the dimethylaminobenzoate and the pentaene chromophores, and therefore established the 15R configuration. Thus, by considering the relative configurations of the remaining stereogenic centers as derived from X-ray crystallography and ROESY experiments, the absolute stereochemistry of the strevertenes is established as 2R, 3S, 5S, 7S, 11R, 13R, 14R, 15R, 26S and 27R.
Guo
J
J
Department of Chemistry, Columbia University, New York, NY 10027, USA.
Schlingmann
G
G
Carter
G T
GT
Nakanishi
K
K
Berova
N
N
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D018942:Macrolides; D011090:Polyenes / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism; D013306:Streptomycetaceae / Q000737:chemistry
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D018942:Macrolides; D011090:Polyenes; D011108:Polymers; C024617:polyol