Regio- and stereoselective hydrogenation of 2'-demethoxy-2'-methyldehydrogriseofulvin, a symmetrical substrate, to (+)-2'-demethoxy-2'-methylgriseofulvin with a cell-free system of Streptomyces cinereocrocatus.
Enzymatic hydrogenation of 2'-demethoxy-2'-methyldehydrogriseofulvin (5) with a cell-free system of Streptomyces cinereocrocatus afforded (+)-2'-demethoxy-2'-methylgriseofulvin (6). The structure of 6 was determined on the basis of comparisons of the proton nuclear magnetic resonance spectrum, mass spectrum, and circular dichroism with those of a standard specimen which was synthesized chemically. The results demonstrated that when the 2'-position of (-)-dehydrogriseofulvin was substituted with a methyl group, its hydrogenation with the cell-free system occurred stereoselectively at the 5',6'-position.
Oda
T
T
Kyoritsu College of Pharmacy, Tokyo, Japan.
Hashimoto
H
H
Sato
Y
Y
D006118:Griseofulvin / Q000031:analogs & derivatives* / Q000378:metabolism; D006865:Hydrogenation; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism*
C064177:2'-demethoxy-2'-methyldehydrogriseofulvin; C064178:2'-demethoxy-2'-methylgriseofulvin; D006118:Griseofulvin