• 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

使用甲硫氨酸亚砜还原酶B的一种新同系物对亚砜进行高对映选择性动力学拆分。

Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B.

作者信息

Zhao Yuyan, Jiang Xu, Zhou Shihuan, Tian Jin, Yang Piao, Chen Yanli, Zhang Quan, Xu Xianlin, Chen Yongzheng, Yang Jiawei

机构信息

Department of Biochemistry, School of Preclinical Medicine, Zunyi Medical University, China.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, China.

出版信息

Org Biomol Chem. 2023 Apr 26;21(16):3417-3422. doi: 10.1039/d3ob00402c.

DOI:10.1039/d3ob00402c
PMID:37017279
Abstract

Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic () sulfoxides. This MsrB homologue, named MsrB, was identified from sp. 103DPR2 and showed good activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the configuration were prepared in approximately 50% yield and 92-99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L). This study presents an efficient route for the enzymatic preparation of ()-sulfoxides through kinetic resolution.

摘要

光学纯的亚砜是值得关注的化合物,在各种工业领域有广泛应用。在此,我们报道了一种甲硫氨酸亚砜还原酶B(MsrB)同源物,它对消旋()亚砜的动力学拆分表现出高对映选择性和广泛的底物范围。这种MsrB同源物,命名为MsrB,是从sp. 103DPR2中鉴定出来的,对一系列芳香族、杂芳香族、烷基和硫代烷基亚砜表现出良好的活性和对映选择性。通过在初始底物浓度高达90 mM(11.2 g L)下进行动力学拆分,以约50%的产率和92 - 99%的对映体过量制备了构型为的手性亚砜。本研究提出了一种通过动力学拆分酶法制备() - 亚砜的有效途径。

相似文献

1
Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B.使用甲硫氨酸亚砜还原酶B的一种新同系物对亚砜进行高对映选择性动力学拆分。
Org Biomol Chem. 2023 Apr 26;21(16):3417-3422. doi: 10.1039/d3ob00402c.
2
Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations.为在高底物浓度下制备 (R)-亚砜而鉴定 MsrA 同源物。
Org Biomol Chem. 2019 Mar 27;17(13):3381-3388. doi: 10.1039/c9ob00384c.
3
Engineering of methionine sulfoxide reductase A with simultaneously improved stability and activity for kinetic resolution of chiral sulfoxides.甲硫氨酸亚砜还原酶 A 的工程改造,同时提高了稳定性和活性,用于手性亚砜的动力学拆分。
Int J Biol Macromol. 2024 Mar;260(Pt 1):129540. doi: 10.1016/j.ijbiomac.2024.129540. Epub 2024 Jan 19.
4
Multienzyme Redox System with Cofactor Regeneration for Cyclic Deracemization of Sulfoxides.多酶氧化还原体系与辅因子再生用于手性拆分外消旋砜
Angew Chem Int Ed Engl. 2022 Sep 12;61(37):e202209272. doi: 10.1002/anie.202209272. Epub 2022 Aug 4.
5
Enzymatic kinetic resolution of chiral sulfoxides - an enantiocomplementary approach.手性亚砜的酶动力学拆分——一种对映互补的方法。
Chem Commun (Camb). 2019 Aug 27;55(70):10480-10483. doi: 10.1039/c9cc05470g.
6
Synthesis of Chiral Sulfoxides by A Cyclic Oxidation-Reduction Multi-Enzymatic Cascade Biocatalysis.通过循环氧化还原多酶级联生物催化合成手性亚砜。
Chemistry. 2024 Apr 2;30(19):e202304081. doi: 10.1002/chem.202304081. Epub 2024 Feb 15.
7
Synthesis of Enantioenriched Sulfoxides by an Oxidation-Reduction Enzymatic Cascade.通过氧化还原酶级联反应合成对映体富集的亚砜。
Chemistry. 2022 Nov 2;28(61):e202201997. doi: 10.1002/chem.202201997. Epub 2022 Aug 31.
8
Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides.利用一株罗特氏菌(Rhodococcus sp. strain)实现外消旋砜的高生产力和对映选择性拆分,替代前手性砜的生物氧化,以高效生产对映纯砜。
Bioresour Technol. 2011 Jan;102(2):1537-42. doi: 10.1016/j.biortech.2010.08.025. Epub 2010 Aug 11.
9
Efficient asymmetric oxidation of sulfides and kinetic resolution of sulfoxides catalyzed by a vanadium-salan system.钒-萨伦体系催化硫化物的高效不对称氧化及亚砜的动力学拆分
J Org Chem. 2004 Nov 26;69(24):8500-3. doi: 10.1021/jo040221d.
10
Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases.发展一种简单的高通量筛选方法用于对映选择性亚砜还原酶的定向进化。
Chem Commun (Camb). 2020 May 19;56(40):5386-5388. doi: 10.1039/d0cc01660h.

引用本文的文献

1
An Iron-Catalyzed Sustainable Functional Group Transfer Strategy for In-Water Transformation of Organic Sulfides to Sulfoxides by a Hydroxylamine-Derived Oxidant.一种铁催化的可持续官能团转移策略:通过羟胺衍生的氧化剂在水中将有机硫化物转化为亚砜
ChemSusChem. 2025 Jun 17;18(12):e202500032. doi: 10.1002/cssc.202500032. Epub 2025 Apr 11.
2
Characterization and mechanism investigation of salt-activated methionine sulfoxide reductase A from halophiles.嗜盐菌盐激活型甲硫氨酸亚砜还原酶A的表征及作用机制研究
iScience. 2024 Aug 23;27(9):110806. doi: 10.1016/j.isci.2024.110806. eCollection 2024 Sep 20.