Baker's yeast: production of D- and L-3-hydroxy esters

被引:34
作者
Dahl, AC [1 ]
Madsen, JO [1 ]
机构
[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark
关键词
D O I
10.1016/S0957-4166(98)00471-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Baker's yeast grown under oxygen limited conditions and used in the reduction of 3-oxo esters results in a shift of the stereoselectivity of the yeast towards D-hydroxy esters as compared with ordinary baker's yeast. The highest degree of stereoselectivity was obtained with growing yeast or yeast harvested while growing. In contrast, the stereoselectivity was shifted towards L-hydroxy esters when the oxo esters were added slowly to ordinary baker's yeast supplied with gluconolactone as co-substrate. The reduction rate with gluconolactone was increased by active aeration. Ethyl L-(S)-3-hydroxybutanoate was afforded in >99% ee. Both enantiomers of ethyl 3-hydroxypentanoate, D-(R) in 96% ee and L-(S) in 93% ee, and of ethyl 4-chloro-3-hydroxybutanoate, D-(S) in 98% ee and L-(R) in 94% ee, were obtained. The results demonstrate that the stereoselectivity of baker's yeast can be controlled to a large extent without the use of inhibitors, heat treatment, etc. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4395 / 4417
页数:23
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