Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

被引：44

作者：

Kiyota, H ^{[1
]}

Higashi, E ^{[1
]}

Koike, T ^{[1
]}

Oritani, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(01)00169-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (+/-)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (+/-)-3 (E=370) and hydrolysis of the corresponding acetate (E=41). Resolution of (+/-)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1035 / 1038

页数：4

共 22 条

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Beale MH, 1998, NAT PROD REP, V15, P533

[2] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].