作为立体选择性酮类生物还原的全细胞生物催化剂

Q2 Chemical Engineering
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 ,&nbsp;László Nagy-Győr ,&nbsp;Róbert Örkényi ,&nbsp;Zsófia Molnár ,&nbsp;Szabolcs Kohári ,&nbsp;Balázs Erdélyi ,&nbsp;Zsuzsanna Nagymáté ,&nbsp;Csaba Romsics ,&nbsp;Csaba Paizs ,&nbsp;László Poppe ,&nbsp;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 ,&nbsp;László Nagy-Győr ,&nbsp;Róbert Örkényi ,&nbsp;Zsófia Molnár ,&nbsp;Szabolcs Kohári ,&nbsp;Balázs Erdélyi ,&nbsp;Zsuzsanna Nagymáté ,&nbsp;Csaba Romsics ,&nbsp;Csaba Paizs ,&nbsp;László Poppe ,&nbsp;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}
引用次数: 8

摘要

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%]。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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

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%].

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Journal of Molecular Catalysis B-enzymatic
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
0
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信