Asymmetric Reduction of #alpha#-Keto Esters and #alpha#-Diketones with a Bakers' Yeast Keto Ester Reductase

Yasushi Kawai; Kouichi Hida; Munekazu Tsujimoto; Shin-ichi Kondo; Kazutada Kitano; Kaoru Nakamura; Atsuyoshi Ohno

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Asymmetric Reduction of #alpha#-Keto Esters and #alpha#-Diketones with a Bakers' Yeast Keto Ester Reductase

机译：贝克酵母酮酮酯还原酶对＃alpha＃-酮酯和＃alpha＃-二酮的不对称还原

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Optically pure #alpha#-hydroxy esters and #alpha#-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of #alpha#-keto esters affords the corresponding (S) -or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An #alpha#-veto alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of #alpha#-diketones affords the corresponding (S)-2-hydroxy ketones regio-and stereo selectively.

机译：通过用从面包酵母中分离的酮酯还原酶（YKER-1）还原相应的酮，已经合成了光学纯的＃α＃-羟基酯和＃α＃-羟基酮。＃α＃-酮酯的还原选择性地提供相应的（S）-或（R）-羟基酯，其中立体化学过程取决于羰基上烷基取代基的链长。 -α-否决链烷酸酯提供相应的（S）-羟基酯，而长链烷酸酯产生相应的（R）-羟基酯。＃α＃-二酮的还原选择性地提供相应的（S）-2-羟基酮区域和立体。

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《Bulletin of the Chemical Society of Japan》 |1999年第1期|共4页
作者
Yasushi Kawai; Kouichi Hida; Munekazu Tsujimoto; Shin-ichi Kondo; Kazutada Kitano; Kaoru Nakamura; Atsuyoshi Ohno;
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正文语种 eng
中图分类化学;化学工业;
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1. Asymmetric Reduction of #alpha#-Keto Esters and #alpha#-Diketones with a Bakers' Yeast Keto Ester Reductase [J] . Yasushi Kawai, Kouichi Hida, Munekazu Tsujimoto, Bulletin of the Chemical Society of Japan . 1999,第1期

机译：贝克酵母酮酮酯还原酶对＃alpha＃-酮酯和＃alpha＃-二酮的不对称还原
2. INTRODUCTION OF PLURAL ASYMMETRIC CENTERS BY A BETA-KETO ESTER REDUCTASE FROM BAKERS YEAST [J] . Kawai Y., Nakamura K., Ohno A., Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 1995,第4期

机译：来自Bakers酵母的β-酮酯还原酶引入多不对称中心
3. Asymmetric reduction of alpha-keto esters with thermophilic actinomycete: purification and characterization of alpha-keto ester reductase from Streptomyces thermocyaneoviolaceus IFO 14271 [J] . Ishihara K., Hamada H., Nakamura K., Journal of molecular catalysis, B. Enzymatic . 2000,第4期

机译：用嗜热放线菌不对称还原α-酮酯：热链霉菌IFO 14271的α-酮酯还原酶的纯化和表征
4. Synthesis of (R)-(-)-Mandelic Acid Methyl Ester by Asymmetric Reduction of Methyl Benzoylformate with Yeast Cells [C] . Zhimin Ou, Yong Liu, Yinkang Nan Biomedical Engineering and Biotechnology (iCBEB), 2012 International Conference on . 2012

机译：酵母细胞不对称还原苯甲酰甲酸酯合成（R）-（-）-扁桃酸甲酯
5. Baker's yeast beta-keto ester reductions: Whole cell biocatalysts with improved stereoselectivity by recombinant DNA techniques. [D] . Rodriguez Giordano, Sonia. 2000

机译：贝克酵母的β-酮酸酯减少：通过重组DNA技术提高立体选择性的全细胞生物催化剂。
6. Asymmetric reduction of ketones and β-keto esters by (S)-1-phenylethanol dehydrogenase from denitrifying bacterium Aromatoleum aromaticum [O] . A. Dudzik, W. Snoch, P. Borowiecki, -1

机译：脱硝细菌芳烃中的（S）-1-苯基乙醇脱氢酶不对称还原酮和β-酮酯
7. Asymmetric Reduction of Cyclic Diketones and Keto-Esters with Baker's Yeast and Its Application to the Synthesis of Bioactive Molecules. [O] . Takeshi KITAHARA 1994

机译：具有面包师酵母的环状二酮和酮酯的不对称还原及其在生物活性分子的合成中的应用。
8. Asymmetric Reduction of Alpha-Keto Esters with Potassium 9-O-(1,2:5,6-Di-O-Isopropylidene-Alpha-D-Glucofuranosyl)-9- Boratabicyclo(3.3.1)Nonane. Chiral Synthesis of Alpha-Hydroxy Esters with Optical Purity Approaching 100% ee [R] . Brown, H. C., Cho, B. T., Park, W. S. 1986

机译：用9-O-（1,2：5,6-二-O-异亚丙基-α-D-葡呋喃糖基）-9-硼代三环（3.3.1）壬烷不对称还原α-酮基酯。具有光学纯度接近100％ee的α-羟基酯的手性合成

Asymmetric Reduction of #alpha#-Keto Esters and #alpha#-Diketones with a Bakers' Yeast Keto Ester Reductase

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