Shimizu S, Kataoka M, Kita K
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan.
Ann N Y Acad Sci. 1998 Dec 13;864:87-95. doi: 10.1111/j.1749-6632.1998.tb10291.x.
Production of chiral 4-chloro-3-hydroxybutanoate ethyl esters (CHBE) was performed through microbial asymmetric reduction of 4-chloroacetoacetate ethyl ester (CAAE). The enzymes reducing CAAE to (R)- and (S)-CHBE were found to be produced by Sporobolomyces salmonicolor and Candida magnoliae, respectively. The enzyme of S. salmonicolor is a novel NADPH-dependent aldehyde reductase (AR) belonging to the aldo-keto reductase superfamily. When AR-overproducing Escherichia coli transformant cells or C. magnoliae cells were incubated in an organic solvent-water two-phase system, 300 or 90 mg/mL of CAAE was almost stoichiometrically converted to (R)- or (S)-CHBE (> 92% ee), respectively.
通过对4-氯乙酰乙酸乙酯（CAAE）进行微生物不对称还原反应来制备手性4-氯-3-羟基丁酸乙酯（CHBE）。结果发现，将CAAE还原为（R）-CHBE和（S）-CHBE的酶分别由浅红锁掷酵母和木兰假丝酵母产生。浅红锁掷酵母的酶是一种新型的依赖NADPH的醛还原酶（AR），属于醛酮还原酶超家族。当过量表达AR的大肠杆菌转化细胞或木兰假丝酵母细胞在有机溶剂-水两相体系中孵育时，300或90 mg/mL的CAAE分别几乎以化学计量比转化为（R）-或（S）-CHBE（对映体过量值>92%）。
