Enzymatic processes for the production of D-pantoyl lactone and related optically active hydroxylated compounds

用于生产 D-泛酰内酯和相关光学活性羟基化化合物的酶法

基本信息

批准号：
62560102
负责人：
SHIMIZU Sakayu
金额：
$ 1.28万
依托单位：
Kyoto University
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1987
资助国家：
日本
起止时间：
1987 至 1988
项目状态：
已结题

项目摘要

The efficient enzymatic conversion of ketopantoyl lactone to D-(-)-pantoyl lactone was found to take place on incubation with washed cells of Candida parapsilosis IFO 0708 or Rhodotorula minuta IFO 0920. They showed high conversion activity when grown with 5% corn steep liquor and 5% glucose, sucrose,maltose or glycerol.Under suitable reaction conditions the amounts of D-(-)-pantoyl lactone reached 49.5g/l(94.4%e.e; molar yield,99%) and 89.9g/l(80.4%e.e; molar yield,99%)with cells of R.minuta and C.parapsilosis,respectively.A novel enzymatic process for the synthesis of D(-)-pantoyl lactone from a racemic mixture of pantoyllactone was also developed.The process involves the stereospecific oxidation of the L(+)-isomer of pantoyl lactoneto ketopantoyl lactone followed by its asymmetric reduction to the D(-)-isomer. The oxidation is carried out with cells of Nocardia asteroides AKU 2103 as the catalyst, which convert only the L(+)-isomer of pantoyl lactone to keto-pantoyl lactone without any modification of the remaining D(-)-isomer.With 80gl^<-1> DL-pantoyl lactone as the substrate,>90%of the added L(+)-isomer was converted to ketopantoyl lactone under the optimum reaction conditions. The ketopantoyl lactone that accumulated in the reaction mixture was almost specifically converted to the D(-)-isomer of pantoyl lactone on incubation with cells of Candida parapsilosis IFO 0784. Scince this process is simple and requires no reracemization step, which is necessary for conventional chemical resolution, it is highly advantageous for the practical synthesis of D(-)-pantoyl lactone.

发现酮氨基酰基二酮向D - （ - ） - Pantoyl内酯的有效酶转化是在与洗涤的Parapapsilosis Ifo 0708或Rhodotorula Minuta Ifo 0920孵育时发生的。 D - （ - ） - Pantoyl lactone达到49.5G/L（94.4％E.E;摩尔产量，99％）和89.9g/L（89.9g/L（80.4％E.E E.E;摩尔的产量，99％），分别具有r.minuta和parapapasilisois的细胞。该过程涉及Pantoyl lactoneto ketopantoyl Lactone的L（+） - 异构体的立体氧化，然后其对D（ - ） - 异构体的不对称还原。氧化是用诺卡氏症的星际心脏Aku 2103细胞作为催化剂进行的，仅将Pantoyl lactone的L（+） - 异构体转换为Keto-Pantoyl Lactone，而没有任何修改的D（ - ） - isomer.with 80gl^<-1> dl-dl-Pantoyl lactoyl lactonate subs subs subs subs subsemant subs subs subs subs subs subs subs subs suptratation）在最佳反应条件下，将L（+） - 异构体转化为酮烷酰基内酯。 The ketopantoyl lactone that accumulated in the reaction mixture was almost specifically converted to the D(-)-isomer of pantoyl lactone on incubation with cells of Candida parapsilosis IFO 0784. Scince this process is simple and requires no reracemization step, which is necessary for conventional chemical resolution, it is highly advantageous for the practical synthesis of D(-)-pantoyl lactone.