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

被引：3

作者：

Okazaki, R

Oritani, T ^{[1
]}

Hara, Y

Yamamoto, H

机构：

[1] Tohoku Univ, Grad Sch Agr Sci, Div Life Sci, Lab Appl Bioorgan Chem, Sendai, Miyagi 9818555, Japan

[2] Niigata Univ, Fac Agr, Dept Appl Biol Chem, Niigata 9502181, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2001年 / 65卷 / 04期

关键词：

xanthoxin; xanthoxin acid; Cunninghamella echinulata; Cercospora cruenta; microbial hydroxylation;

D O I：

10.1271/bbb.65.943

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Microbial hydroxylation of (+/-)-(2 Z, 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 (-)-santhoxin acid (4a), and (+)- and (-)-epi-xanthoxin acid (5a) bg an HPLC an: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.

引用

页码：943 / 946

页数：4

共 10 条

[1]

Addicott FT, 1983, ABSCISIC ACID

[2]

FIRN RD, 1972, PLANTA, V102

[3] SYNTHESIS OF OPTICALLY-ACTIVE NATURAL CAROTENOIDS AND STRUCTURALLY RELATED COMPOUNDS .3. SYNTHESIS OF (+)-ABSCISIC ACID,(-)-XANTHOXIN,(-)-LOLIOLIDE, (-)-ACTINIDIOLIDE, AND (-)-DIHYDROACTINIDIOLIDE [J].