PREPARATION OF BOTH ENANTIOMERS OF MALIC AND CITRAMALIC ACID AND OTHER HYDROXYSUCCINIC ACID-DERIVATIVES BY STEREOSPECIFIC HYDRATIONS OF CIS OR TRANS 2-BUTENE-1,4-DIOIC ACIDS WITH RESTING CELLS OF CLOSTRIDIUM-FORMICOACETICUM

被引:9
作者
ECK, R [1 ]
SIMON, H [1 ]
机构
[1] TECH UNIV MUNICH,LEHRSTUHL ORGAN CHEM & BIOCHEM,D-85747 GARCHING,GERMANY
关键词
D O I
10.1016/S0040-4020(01)85678-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(R)-Malic, (S)-malic, (R)-citramalic, (S)-citramalic, (2R,3S)-2-hydroxy-3-methylsuccinic and (2R,3S)-2,3-dimethyl-2-hydroxysuccinic acid were prepared on scales up to 25 mmol by stereospecific addition of water to different 2-butene-1,4-dioic acid derivatives catalyzed by resting cells of Clostridium formicoaceticum (Scheme 1). The (3R)-monodeuterio (R)- and (S)-malic acid as well as (R)- and (S)-citramalic acid were prepared using freeze-dried cells in (H2O)-H-2-buffer. The stereochemical purity of the products was in most cases greater than or equal to 99%.
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页码:13641 / 13654
页数:14
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