小球藻对3-氧戊酸甲酯的不对称还原

Fumiki Yoshizako, Takayuki Kuramoto, Atsuo Nishimura, Mitsuo Chubachi
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引用次数: 9

摘要

小球藻(Chlorella pyrenoidosa Chick)催化3-氧戊酸甲酯(me3 -oxopen)还原成相应的(S)-(+)-3-羟基酯,对映体过量(ee)达60%。通过增加底物浓度和添加1%的金属盐,即NaCl和KCl (ee为75-78%),可以提高(S)-(+)-3-羟基酯的ee。在此加成后,没有观察到ee向(R)-(−)-3-羟基酯的转移。烯丙醇的加入降低了(S)-(+)-3-羟基酯的化学产率和ee。三种小球藻对me - 3-oxoPen的还原能力存在差异,其中C. pyrenoidosa Chick产(S)-(+)-3-羟基酯,C. regularis和C. vulgaris Beijerinck产(R)-(−)-对映体。特别是,C. regularis在79%的ee中将Me 3-oxoPen转化为(R)-(−)-3-羟基酯,产率为10%。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Asymmetric reduction of methyl 3-oxopentanoate by Chlorella

Chlorella pyrenoidosa Chick catalyzed the reduction of methyl 3-oxopentanoate (Me 3-oxoPen) to the corresponding (S)-(+)-3-hydroxy ester in 60% enantiomeric excess (ee). An improvement of the ee of (S)-(+)-3-hydroxy ester was achieved by increasing substrate concentration and by the addition of 1% metal salts, namely, NaCl and KCl (75–78% ee). No shift of ee toward the (R)-(−)-3-hydroxy ester was observed following this addition. The addition of allyl alcohol brought about a decrease in both the chemical yields and the ee of (S)-(+)-3-hydroxy ester. Differences in the ability to reduce me 3-oxoPen were observed among three strains of Chlorella, of which C. pyrenoidosa Chick yields the (S)-(+)-3-hydroxy ester but C. regularis and C. vulgaris Beijerinck yield (R)-(−)-enantiomer. In particular, C. regularis transformed Me 3-oxoPen to (R)-(−)-3-hydroxy ester in 79% ee, with a 10% yield.

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