Enzymatic esterification of lavandulol – a partial kinetic resolution of (S)-lavandulol and preparation of optically enriched (R)-lavandulyl acetate

被引：0

作者：

Hannah Cross

Ray Marriott

Gideon Grogan

机构：

[1] University of York,York Structural Biology Laboratory, Department of Chemistry

[2] Botanix Ltd.,undefined

来源：

Biotechnology Letters | 2004年 / 26卷

关键词：

biotransformation; lavandulol; lipase; resolution; terpene;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

The asymmetric esterification of the racemic primary alcohol lavandulol was achieved using lipase B from Candida antarctica and acetic acid as acyl donor in 80% yield. The enantioselectivity of the process was characterised, and a preparative resolution of 25 mm racemic lavandulol, stopped at approx. 55% conversion, yielded (S)-lavandulol in 42% yield and 52% e.e. and (R)-lavandulyl acetate in 51% yield and 48% e.e.

引用

页码：457 / 460

页数：3

共 37 条

[1] Enzymatic esterification of lavandulol -: a partial kinetic resolution of (S)-lavandulol and preparation of optically enriched (R)-lavandulyl acetate
Cross, H
Marriott, R
Grogan, G
BIOTECHNOLOGY LETTERS, 2004, 26 (05) : 457 - 460
[2] Enzymatic transesterification of racemic lavandulol: preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate
Zada, A
Harel, M
TETRAHEDRON-ASYMMETRY, 2004, 15 (15) : 2339 - 2343
[3] A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-Methylbutanoate, and (+)-Lavandulyl Senecioate through Orthoester Johnson-Claisen Rearrangement
Fernandes, Rodney A.
Chowdhury, Asim K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) : 5165 - 5170
[4] A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride:: simple preparation of enantiomerically pure (R)-lavandulol
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TETRAHEDRON-ASYMMETRY, 2006, 17 (02) : 230 - 233
[5] PREPARATION OF THE OPTICALLY ACTIVE ISOMERS OF S-BENZYLHOMOCYSTEINE BY ENZYMATIC RESOLUTION
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JOURNAL OF BIOLOGICAL CHEMISTRY, 1949, 180 (02) : 571 - 574
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Li, Hongxia
Chen, Zhongsheng
Le, Zhanggao
Xie, Zongbo
Jingxi Huagong/Fine Chemicals, 2022, 39 (06): : 1212 - 1217
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Liu, M
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[8] Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution
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Hanefeld, Ulf
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 85-86 : 239 - 242
[9] Enzymatic hydrolytic resolution of (R,S)-tropic acid esters and (R,S)-ethyl α-methoxyphenyl acetate in biphasic media
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[10] Kinetic Resolution of (R,S)-2-Butanol Using Enzymatic Synthesis of Esters
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