Microbial hydroxylation of (+/-)- and (-)-(2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid into (+/-)- and (-)-xanthoxin acid by Cunninghamella echinulata.
Microbial hydroxylation of (+/-)-(2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid (3a) with Cercospora cruenta, a fungus producing (+)-abscisic acid, gave a four-stereoisomeric mixture consisting of (+)- and (-)-xanthoxin acid (4a), and (+)- and (-)-epi-xanthoxin acid (5a) by an HPLC analysis with a chiral column. Screening of the microorganisms capable of oxidizing (+/-)-3a showed that Cunninghamella echinulata stereoselectively oxidized (+/-)-3a to xanthoxin acid (4a) with the some degree of enantioselectivity as (-)-3a to (-)-4a.
Okazaki
R
R
Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Oritani
T
T
Hara
Y
Y
Yamamoto
H
H
D002338:Carotenoids; D002855:Chromatography, Thin Layer; D020093:Cunninghamella / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D006900:Hydroxylation; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
C437409:5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid; D005231:Fatty Acids, Unsaturated; D012717:Sesquiterpenes; C012475:xanthoxin; D002338:Carotenoids