A CHEMOENZYMATIC APPROACH TO OPTICALLY-ACTIVE 3-(4-METHOXYCARBONYL)PHENYL-2-METHYL-1-PROPANOLS

被引：9

作者：

GAMALEVICH, GD ^{[1
]}

IGNATENKO, AV ^{[1
]}

SEREBRYAKOV, EP ^{[1
]}

VOISHVILLO, NE ^{[1
]}

机构：

[1] ND ZELINSKII INST ORGAN CHEM,MOSCOW 117913,RUSSIA

来源：

RUSSIAN CHEMICAL BULLETIN | 1995年 / 44卷 / 04期

关键词：

PANCREATIC LIPASE; (+/-)-3-(4-METHOXYCARBONYL)PHENYL-2-METHYL ACETATE; ENZYMATIC HYDROLYSIS; 3-(4-METHOXYCARBONYL)PHENYL-2-METHYL-2-PROPEN-1-OL; YEAST REDUCTION;

D O I：

10.1007/BF00698514

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (+/-)-1, the hydrolysis of its acetate, (+/-)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22-27 %), and could not be increased beyond ee 33 % by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermenting Saccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41-90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (+/-)-2 produces preferably (R)-1.

引用

页码：743 / 748

页数：6

共 22 条

[1] A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].