Viktória Bódai , László Nagy-Győr , Róbert Örkényi , Zsófia Molnár , Szabolcs Kohári , Balázs Erdélyi , Zsuzsanna Nagymáté , Csaba Romsics , Csaba Paizs , László Poppe , Gábor Hornyánszky
{"title":"作为立体选择性酮类生物还原的全细胞生物催化剂","authors":"Viktória Bódai , László Nagy-Győr , Róbert Örkényi , Zsófia Molnár , Szabolcs Kohári , Balázs Erdélyi , Zsuzsanna Nagymáté , Csaba Romsics , Csaba Paizs , László Poppe , Gábor Hornyánszky","doi":"10.1016/j.molcatb.2016.11.003","DOIUrl":null,"url":null,"abstract":"<div><p>Newly isolated strains of <em>Wickerhamomyces subpelliculosus</em> 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 <strong>1a</strong>, 2-heptanone <strong>1b</strong>, phenylacetone <strong>1c</strong>, 3,4-dimethoxyphenylacetone <strong>1d</strong> and 1-cyclopropyl-2-(2-methoxy-4-nitrophenoxy)ethanone <strong>1e</strong>. Our study is the first report on application of <em>W. subpelliculosus</em> 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 <em>W. subpelliculosus</em> showed diverse characteristics, including optimal pH, temperature and organic solvent tolerance. Bioreductions of phenylacetone <strong>1c</strong> applying glucose as cosubstrate under various mild conditions resulted (<em>S</em>)-1-phenylpropanol [(<em>S</em>)-<strong>2c</strong>] in good to excellent conversion (<em>c</em> <!-->=<!--> <!-->63.4%–99.9%) with excellent enantiomeric excess [<em>ee</em><sub>(<em>S</em>)-<strong>2c</strong></sub> <!-->=<!--> <!-->98.7%–99.8%].</p></div>","PeriodicalId":16416,"journal":{"name":"Journal of Molecular Catalysis B-enzymatic","volume":"134 ","pages":"Pages 206-214"},"PeriodicalIF":0.0000,"publicationDate":"2016-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.molcatb.2016.11.003","citationCount":"8","resultStr":"{\"title\":\"Wickerhamomyces subpelliculosus as whole-cell biocatalyst for stereoselective bioreduction of ketones\",\"authors\":\"Viktória Bódai , László Nagy-Győr , Róbert Örkényi , Zsófia Molnár , Szabolcs Kohári , Balázs Erdélyi , Zsuzsanna Nagymáté , Csaba Romsics , Csaba Paizs , László Poppe , Gábor Hornyánszky\",\"doi\":\"10.1016/j.molcatb.2016.11.003\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Newly isolated strains of <em>Wickerhamomyces subpelliculosus</em> 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 <strong>1a</strong>, 2-heptanone <strong>1b</strong>, phenylacetone <strong>1c</strong>, 3,4-dimethoxyphenylacetone <strong>1d</strong> and 1-cyclopropyl-2-(2-methoxy-4-nitrophenoxy)ethanone <strong>1e</strong>. Our study is the first report on application of <em>W. subpelliculosus</em> 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 <em>W. subpelliculosus</em> showed diverse characteristics, including optimal pH, temperature and organic solvent tolerance. Bioreductions of phenylacetone <strong>1c</strong> applying glucose as cosubstrate under various mild conditions resulted (<em>S</em>)-1-phenylpropanol [(<em>S</em>)-<strong>2c</strong>] in good to excellent conversion (<em>c</em> <!-->=<!--> <!-->63.4%–99.9%) with excellent enantiomeric excess [<em>ee</em><sub>(<em>S</em>)-<strong>2c</strong></sub> <!-->=<!--> <!-->98.7%–99.8%].</p></div>\",\"PeriodicalId\":16416,\"journal\":{\"name\":\"Journal of Molecular Catalysis B-enzymatic\",\"volume\":\"134 \",\"pages\":\"Pages 206-214\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2016-12-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.molcatb.2016.11.003\",\"citationCount\":\"8\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Molecular Catalysis B-enzymatic\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1381117716302168\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Chemical Engineering\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Catalysis B-enzymatic","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1381117716302168","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemical Engineering","Score":null,"Total":0}
Wickerhamomyces subpelliculosus as whole-cell biocatalyst for stereoselective bioreduction of ketones
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%].
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.