Wickerhamomyces subpelliculosus as whole-cell biocatalyst for stereoselective bioreduction of ketones

Q2 Chemical Engineering Journal of Molecular Catalysis B-enzymatic Pub Date : 2016-12-01 DOI:10.1016/j.molcatb.2016.11.003

Viktória Bódai , László Nagy-Győr , Róbert Örkényi , Zsófia Molnár , Szabolcs Kohári , Balázs Erdélyi , Zsuzsanna Nagymáté , Csaba Romsics , Csaba Paizs , László Poppe , Gábor Hornyánszky

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引用次数: 8

Abstract

Newly isolated strains of Wickerhamomyces subpelliculosus were recognized as excellent whole-cell biocatalyst for bioreduction of various ketones. The biocatalytic properties of the new strains were demonstrated in this study by stereoselective bioreduction of acetophenone 1a, 2-heptanone 1b, phenylacetone 1c, 3,4-dimethoxyphenylacetone 1d and 1-cyclopropyl-2-(2-methoxy-4-nitrophenoxy)ethanone 1e. Our study is the first report on application of W. subpelliculosus as whole-cell biocatalyst for stereoselective bioreduction of prochiral ketones. In these processes, both the freshly harvested cell paste and the lyophilized cell powder were tested as biocatalyst using glucose or 2-propanol at various concentrations as cosubstrates for cofactor regeneration. The newly isolated strains of W. subpelliculosus showed diverse characteristics, including optimal pH, temperature and organic solvent tolerance. Bioreductions of phenylacetone 1c applying glucose as cosubstrate under various mild conditions resulted (S)-1-phenylpropanol [(S)-2c] in good to excellent conversion (c = 63.4%–99.9%) with excellent enantiomeric excess [ee_(S)-2c = 98.7%–99.8%].

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作为立体选择性酮类生物还原的全细胞生物催化剂

新分离的Wickerhamomyces pelicullosus菌株被认为是生物还原多种酮类的优秀全细胞生物催化剂。通过对苯乙酮1a、2-庚酮1b、苯丙酮1c、3,4-二甲氧基苯丙酮1d和1-环丙基-2-(2-甲氧基-4-硝基苯氧基)乙酮1e的立体选择性生物还原，证实了新菌株的生物催化性能。本研究首次报道了包膜藻作为全细胞生物催化剂在前手性酮立体选择性生物还原中的应用。在这些过程中，新鲜收获的细胞膏和冻干的细胞粉作为生物催化剂进行测试，使用不同浓度的葡萄糖或2-丙醇作为辅助因子再生的辅底物。新分离菌株在最适pH、最适温度、耐有机溶剂等方面表现出多样性。在各种温和条件下，以葡萄糖为共底物对苯丙酮1c进行生物还原，结果(S)-1-苯丙醇[(S)-2c]的转化率从良好到优异(c = 63.4%-99.9%)，对映体过量[ee(S)-2c = 98.7%-99.8%]。

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来源期刊

Journal of Molecular Catalysis B-enzymatic 生物-生化与分子生物学

CiteScore

2.58

自引率

0.00%

发文量

审稿时长

3.4 months

期刊介绍： Journal of Molecular Catalysis B: Enzymatic is an international forum for researchers and product developers in the applications of whole-cell and cell-free enzymes as catalysts in organic synthesis. Emphasis is on mechanistic and synthetic aspects of the biocatalytic transformation. Papers should report novel and significant advances in one or more of the following topics; Applied and fundamental studies of enzymes used for biocatalysis; Industrial applications of enzymatic processes, e.g. in fine chemical synthesis; Chemo-, regio- and enantioselective transformations; Screening for biocatalysts; Integration of biocatalytic and chemical steps in organic syntheses; Novel biocatalysts, e.g. enzymes from extremophiles and catalytic antibodies; Enzyme immobilization and stabilization, particularly in non-conventional media; Bioprocess engineering aspects, e.g. membrane bioreactors; Improvement of catalytic performance of enzymes, e.g. by protein engineering or chemical modification; Structural studies, including computer simulation, relating to substrate specificity and reaction selectivity; Biomimetic studies related to enzymatic transformations.