• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

反转水解酶及其在手性转化生物转化中的应用。

Inverting hydrolases and their use in enantioconvergent biotransformations.

机构信息

Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

出版信息

Trends Biotechnol. 2013 Aug;31(8):468-78. doi: 10.1016/j.tibtech.2013.05.005. Epub 2013 Jun 25.

DOI:10.1016/j.tibtech.2013.05.005
PMID:23809848
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3725421/
Abstract

Owing to the more abundant occurrence of racemic compounds compared to prochiral or meso forms, most enantiomerically pure products are obtained via racemate resolution. This review summarizes (chemo)enzymatic enantioconvergent processes based on the use of hydrolytic enzymes, which are able to invert a stereocenter during catalysis that can overcome the 50%-yield limitation of kinetic resolution. Recent developments are presented in the fields of inverting or retaining sulfatases, epoxide hydrolases and dehalogenases, which allow the production of secondary alcohols or vicinal diols at a 100% theoretical yield from a racemate via enantioconvergent processes.

摘要

由于外消旋化合物比前手性或内消旋形式更丰富,因此大多数对映体纯的产物都是通过外消旋拆分得到的。本综述总结了基于使用水解酶的(化学)酶促对映体转化过程,这些酶能够在催化过程中反转一个立体中心,从而克服动力学拆分的 50%产率限制。介绍了反转或保留硫酸酯酶、环氧化物水解酶和脱卤酶领域的最新进展,这些酶可以通过对映体转化过程从外消旋混合物中以 100%理论产率生产仲醇或顺二醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/81786da05dc4/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/38ef236413ed/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/2d5b83e23614/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/81786da05dc4/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/38ef236413ed/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/2d5b83e23614/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bd/3725421/81786da05dc4/gr3.jpg

相似文献

1
Inverting hydrolases and their use in enantioconvergent biotransformations.反转水解酶及其在手性转化生物转化中的应用。
Trends Biotechnol. 2013 Aug;31(8):468-78. doi: 10.1016/j.tibtech.2013.05.005. Epub 2013 Jun 25.
2
New enzymes for biotransformations: microbial alkyl sulfatases displaying stereo- and enantioselectivity.用于生物转化的新型酶:具有立体和对映选择性的微生物烷基硫酸酯酶
Trends Biotechnol. 2007 Feb;25(2):83-8. doi: 10.1016/j.tibtech.2006.11.006. Epub 2006 Dec 5.
3
Microbial epoxide hydrolases for preparative biotransformations.用于制备性生物转化的微生物环氧化物水解酶。
Curr Opin Biotechnol. 2001 Dec;12(6):552-8. doi: 10.1016/s0958-1669(01)00262-2.
4
Epoxide hydrolase-mediated enantioconvergent bioconversions to prepare chiral epoxides and alcohols.环氧水解酶介导的对映体汇聚生物转化制备手性环氧化物和醇类。
Biotechnol Lett. 2008 Sep;30(9):1509-14. doi: 10.1007/s10529-008-9727-0. Epub 2008 Apr 19.
5
New enzymes for biotransformations.用于生物转化的新型酶。
Curr Opin Chem Biol. 2005 Apr;9(2):181-7. doi: 10.1016/j.cbpa.2005.01.001.
6
Molecular engineering of epoxide hydrolase and its application to asymmetric and enantioconvergent hydrolysis.环氧水解酶的分子工程及其在不对称和对映体汇聚水解中的应用。
Biotechnol Bioeng. 2007 Oct 1;98(2):318-27. doi: 10.1002/bit.21444.
7
Biocatalytic conversion of epoxides.环氧化物的生物催化转化
Curr Opin Biotechnol. 2003 Aug;14(4):414-20. doi: 10.1016/s0958-1669(03)00102-2.
8
Enantioconvergent hydrolysis of m-nitrostyrene oxide at an elevated concentration by Phaseolus vulgaris epoxide hydrolase in the organic/aqueous two-phase system.在有机/水两相体系中,菜豆环氧水解酶在高浓度下对间硝基苯乙烯氧化物进行对映体转化水解。
Lett Appl Microbiol. 2020 Mar;70(3):181-188. doi: 10.1111/lam.13258. Epub 2020 Jan 16.
9
Recent advances on halohydrin dehalogenases-from enzyme identification to novel biocatalytic applications.卤代醇脱卤酶的最新进展——从酶的鉴定到新型生物催化应用
Appl Microbiol Biotechnol. 2016 Sep;100(18):7827-39. doi: 10.1007/s00253-016-7750-y. Epub 2016 Aug 8.
10
Manipulating regioselectivity of an epoxide hydrolase for single enzymatic synthesis of (R)-1,2-diols from racemic epoxides.通过调控环氧化物水解酶的区域选择性,从外消旋环氧化物中单酶合成(R)-1,2-二醇。
Chem Commun (Camb). 2020 Mar 3;56(18):2799-2802. doi: 10.1039/d0cc00283f.

引用本文的文献

1
Hijacking Chemical Reactions of P450 Enzymes for Altered Chemical Reactions and Asymmetric Synthesis.利用 P450 酶的化学反应劫持进行改变的化学反应和不对称合成。
Int J Mol Sci. 2022 Dec 22;24(1):214. doi: 10.3390/ijms24010214.
2
Enzymatic synthesis of enantiopure alcohols: current state and perspectives.对映体纯醇的酶促合成:现状与展望
RSC Adv. 2019 Jan 15;9(4):2102-2115. doi: 10.1039/c8ra09004a. eCollection 2019 Jan 14.
3
Mini Review: Advances in 2-Haloacid Dehalogenases.迷你综述:2-卤代酸脱卤酶的研究进展

本文引用的文献

1
Structure prediction, molecular dynamics simulation and docking studies of D-specific dehalogenase from Rhizobium sp. RC1.来自根瘤菌属RC1的D-特异性脱卤酶的结构预测、分子动力学模拟及对接研究
Int J Mol Sci. 2012 Nov 26;13(12):15724-54. doi: 10.3390/ijms131215724.
2
One-pot deracemization of sec-alcohols: enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases.仲醇的一锅法去消旋化:使用立体互补硫酸酯酶对烷基硫酸盐进行对映收敛性酶促水解
Angew Chem Int Ed Engl. 2013 Mar 11;52(11):3277-9. doi: 10.1002/anie.201209946. Epub 2013 Feb 10.
3
Engineering enzyme stability and resistance to an organic cosolvent by modification of residues in the access tunnel.
Front Microbiol. 2021 Oct 15;12:758886. doi: 10.3389/fmicb.2021.758886. eCollection 2021.
4
The Unexplored Importance of Fleeting Chiral Intermediates in Enzyme-Catalyzed Reactions.酶催化反应中瞬息手性中间物的未探索重要性。
J Am Chem Soc. 2021 Sep 22;143(37):14939-14950. doi: 10.1021/jacs.1c04551. Epub 2021 Sep 7.
5
Synthesis of enantiomerically pure alcohols and amines biocatalytic deracemisation methods.对映体纯醇和胺的合成:生物催化消旋化方法
Catal Sci Technol. 2019 Oct 21;9(20):5487-5503. doi: 10.1039/C9CY01539F. Epub 2019 Sep 3.
6
Machine Learning Enables Selection of Epistatic Enzyme Mutants for Stability Against Unfolding and Detrimental Aggregation.机器学习可用于选择具有抗变性和抗有害聚集稳定性的错义酶突变体。
Chembiochem. 2021 Mar 2;22(5):904-914. doi: 10.1002/cbic.202000612. Epub 2020 Nov 17.
7
Resolution of Atropisomeric Cyclic Catechol Monoether -Sulfate Esters by a Molluscan Sulfatase.利用软体动物硫酸酯酶拆分阻转异构环状儿茶酚单醚硫酸酯
ACS Omega. 2018 Jul 31;3(7):7771-7775. doi: 10.1021/acsomega.7b01899. Epub 2018 Jul 12.
8
Improved activity of lipase immobilized in microemulsion-based organogels for (, )-ketoprofen ester resolution: Long-term stability and reusability.用于(,)-酮洛芬酯拆分的固定在微乳液基有机凝胶中的脂肪酶活性提高:长期稳定性和可重复使用性。
Biotechnol Rep (Amst). 2015 Apr 16;7:1-8. doi: 10.1016/j.btre.2015.04.003. eCollection 2015 Sep.
9
Stereochemistry and Mechanism of Enzymatic and Non-Enzymatic Hydrolysis of Benzylic -Sulfate Esters.苄基硫酸酯的酶促和非酶促水解的立体化学及机理
European J Org Chem. 2014 Jun 1;2014(18):3930-3034. doi: 10.1002/ejoc.201402211.
10
A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.一种适用于对映选择性环氧化合物开环反应的广泛适用且实用的低聚(水杨醛缩邻氨基酚)钴催化剂。
Tetrahedron. 2014 Jul 8;70(27-28):4165-4180. doi: 10.1016/j.tet.2014.03.043.
通过修饰通道内的残基来设计酶的稳定性及对有机助溶剂的抗性。
Angew Chem Int Ed Engl. 2013 Feb 11;52(7):1959-63. doi: 10.1002/anie.201206708. Epub 2013 Jan 9.
4
Stereochemistry of LinB-catalyzed biotransformation of δ-HBCD to 1R,2R,5S,6R,9R,10S-pentabromocyclododecanol.LinB 催化 δ-HBCD 对映体选择性生物转化为 1R,2R,5S,6R,9R,10S-五溴环十二烷醇的立体化学。
Chemosphere. 2013 Feb;90(6):1911-9. doi: 10.1016/j.chemosphere.2012.10.019. Epub 2012 Nov 21.
5
Structure and mechanism of an inverting alkylsulfatase from Pseudomonas sp. DSM6611 specific for secondary alkyl sulfates.假单胞菌 DSM6611 中一种反转烷基亚硫酸酯酶的结构与机制,该酶特异性作用于次级烷基亚硫酸盐。
FEBS J. 2012 Dec;279(23):4374-84. doi: 10.1111/febs.12027. Epub 2012 Nov 7.
6
Haloalkane dehalogenases: biotechnological applications.卤代烷烃脱卤酶:生物技术应用。
Biotechnol J. 2013 Jan;8(1):32-45. doi: 10.1002/biot.201100486. Epub 2012 Sep 11.
7
Obtaining optical purity for product diols in enzyme-catalyzed epoxide hydrolysis: contributions from changes in both enantio- and regioselectivity.在酶促环氧化物水解中获得产物二醇的光学纯度:对映选择性和区域选择性变化的贡献。
Biochemistry. 2012 Sep 25;51(38):7627-37. doi: 10.1021/bi3007725. Epub 2012 Sep 12.
8
Biochemical characterization of a novel haloalkane dehalogenase from a cold-adapted bacterium.一种新型耐冷菌卤代烷脱卤酶的生化特性研究。
Appl Environ Microbiol. 2012 Jul;78(14):4995-8. doi: 10.1128/AEM.00485-12. Epub 2012 May 11.
9
Directed evolution strategies for enantiocomplementary haloalkane dehalogenases: from chemical waste to enantiopure building blocks.定向进化策略在手性互补 haloalkane 脱卤酶中的应用:从化学废物到手性纯砌块。
Chembiochem. 2012 Jan 2;13(1):137-48. doi: 10.1002/cbic.201100579. Epub 2011 Nov 23.
10
A simple enantioconvergent and chemoenzymatic synthesis of optically active α-substituted amides.光学活性α-取代酰胺的一种简单对映汇聚式化学酶促合成方法。
Angew Chem Int Ed Engl. 2011 Nov 4;50(45):10712-5. doi: 10.1002/anie.201105164. Epub 2011 Sep 16.