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

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  • OKAZAKI Ryou
    Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University
  • ORITANI Takayuki
    Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University
  • HARA Yoshihiro
    Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University
  • YAMAMOTO Hirotaka
    Department of Applied Biological Chemitry, Faculty of Agriculture, Niigata University

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  • 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 (±)- and (−)-(2Z,4E)-5-(1',2'-Epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid into (±)- and (−)-Xanthoxin Acid by Cunninghamella echinulata

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説明

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.

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