• 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

利用新分离的菌株产碱杆菌属ECU0401通过对映选择性降解从外消旋体中制备(R)-(-)-扁桃酸及其衍生物。

Preparation of (R)-(-)-mandelic acid and its derivatives from racemates by enantioselective degradation with a newly isolated bacterial strain Alcaligenes sp. ECU0401.

作者信息

He Yu-Cai, Xu Jian-He, Pan Jiang, Ouyang Li-Ming, Xu Yi

机构信息

Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, People's Republic of China.

出版信息

Bioprocess Biosyst Eng. 2008 Aug;31(5):445-51. doi: 10.1007/s00449-007-0181-5. Epub 2007 Dec 12.

DOI:10.1007/s00449-007-0181-5
PMID:18074154
Abstract

An enantioselective mandelate-degrading bacterium, Alcaligenes sp. ECU0401, was newly isolated from soil. By fed-batch culture, (R)-(-)-mandelic acid was successfully prepared in a 5-L fermenter with 32.8% isolated yield and >99.9% enantiomeric excesses (e.e.) from totally 3.04% (w/v) of racemic mandelic acid after 99 h of biotransformation. The optimal reaction pH and temperature were 6.5 and 30 degrees C, respectively. Using the resting cell as a biocatalyst for asymmetric degradation of racemic mandelic acid and chloro-substituted derivatives thereof, (R)-(-)-mandelic acid, (R)-(-)-o-chloromandelic acid, (S)-(+)-m-chloromandelic acid and (S)-(+)-p-chloromandelic acid were recovered with high analytic yields and excellent enantiomeric excesses (e.e. > 99.9%). (R)-(-)-Mandelic acid could also be obtained after 12 h of biotransformation with 41.5% isolated yield and >99.9% e.e.

摘要

从土壤中新分离出一株对映体选择性降解扁桃酸的细菌——产碱菌属ECU0401。通过分批补料培养,在5升发酵罐中,以3.04%(w/v)的外消旋扁桃酸为原料,经过99小时的生物转化,成功制备出(R)-(-)-扁桃酸,分离产率为32.8%,对映体过量值(e.e.)>99.9%。最佳反应pH值和温度分别为6.5和30℃。以静息细胞作为生物催化剂,用于外消旋扁桃酸及其氯代衍生物的不对称降解,可回收得到(R)-(-)-扁桃酸、(R)-(-)-邻氯扁桃酸、(S)-(+)-间氯扁桃酸和(S)-(+)-对氯扁桃酸,分析产率高,对映体过量值优异(e.e.>99.9%)。经过12小时的生物转化,也可获得(R)-(-)-扁桃酸,分离产率为41.5%,e.e.>99.9%。

相似文献

1
Preparation of (R)-(-)-mandelic acid and its derivatives from racemates by enantioselective degradation with a newly isolated bacterial strain Alcaligenes sp. ECU0401.利用新分离的菌株产碱杆菌属ECU0401通过对映选择性降解从外消旋体中制备(R)-(-)-扁桃酸及其衍生物。
Bioprocess Biosyst Eng. 2008 Aug;31(5):445-51. doi: 10.1007/s00449-007-0181-5. Epub 2007 Dec 12.
2
Bioproduction of chiral mandelate by enantioselective deacylation of alpha-acetoxyphenylacetic acid using whole cells of newly isolated Pseudomonas sp. ECU1011.新型假单胞菌 ECU1011 全细胞对α-乙酰氧苯乙酸进行对映选择性去乙酰化反应生物合成手性扁桃酸。
Appl Microbiol Biotechnol. 2010 Mar;86(1):83-91. doi: 10.1007/s00253-009-2286-z. Epub 2009 Oct 16.
3
Screening and immobilization Burkholderia sp. GXU56 lipase for enantioselective resolution of (R,S)-methyl mandelate.筛选和固定化伯克霍尔德氏菌属GXU56脂肪酶用于对映选择性拆分(R,S)-扁桃酸甲酯。
Appl Biochem Biotechnol. 2008 Apr;149(1):79-88. doi: 10.1007/s12010-007-8125-8. Epub 2008 Jan 26.
4
Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750.粪产碱菌ATCC 8750从扁桃腈生产R-(-)-扁桃酸。
Appl Environ Microbiol. 1991 Oct;57(10):3028-32. doi: 10.1128/aem.57.10.3028-3032.1991.
5
Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401.利用嗜粪产碱杆菌 ECU0401 的溴化十六烷基三甲铵透性化细胞对消旋扁桃腈进行生物催化合成(R)-(-)-扁桃酸。
J Ind Microbiol Biotechnol. 2010 Jul;37(7):741-50. doi: 10.1007/s10295-010-0720-y. Epub 2010 Apr 22.
6
Cloning and biochemical properties of a highly thermostable and enantioselective nitrilase from Alcaligenes sp. ECU0401 and its potential for (R)-(-)-mandelic acid production.一株耐热及对映体选择性腈酶的克隆和生化性质及其在(R)-(-)-扁桃酸生产中的应用。
Bioprocess Biosyst Eng. 2011 Mar;34(3):315-22. doi: 10.1007/s00449-010-0473-z. Epub 2010 Oct 20.
7
Integration of newly isolated biocatalyst and resin-based in situ product removal technique for the asymmetric synthesis of (R)-methyl mandelate.新型生物催化剂与基于树脂的原位产物去除技术的整合用于(R)-甲基扁桃酸的不对称合成。
Bioprocess Biosyst Eng. 2010 Sep;33(7):797-804. doi: 10.1007/s00449-009-0401-2. Epub 2009 Dec 23.
8
Optimization of arylacetonitrilase production from Alcaligenes sp. MTCC 10675 and its application in mandelic acid synthesis.从 Alcaligenes sp. MTCC 10675 生产芳基乙腈酶的优化及其在扁桃酸合成中的应用。
Appl Microbiol Biotechnol. 2014 Jan;98(1):83-94. doi: 10.1007/s00253-013-5288-9. Epub 2013 Oct 9.
9
Bioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401.用新分离的产碱杆菌 ECU0401 从乙腈制备羟基乙酸。
Appl Biochem Biotechnol. 2010 Mar;160(5):1428-40. doi: 10.1007/s12010-009-8607-y. Epub 2009 Mar 31.
10
Highly enantioselective oxidation of racemic phenyl-1,2-ethanediol to optically pure (R)-(-)-mandelic acid by a newly isolated Brevibacterium lutescens CCZU12-1.一株新分离短杆菌 CCZU12-1 对外消旋苯乙醇的高效对映选择性氧化制备(R)-(-)-扁桃酸。
Appl Microbiol Biotechnol. 2013 Aug;97(16):7185-94. doi: 10.1007/s00253-013-4989-4. Epub 2013 Jun 5.

引用本文的文献

1
Chiroptical characterization tools for asymmetric small molecules - experimental and computational approaches for electronic circular dichroism (ECD) and anisotropy spectroscopy.用于不对称小分子的手性光表征工具——电子圆二色性(ECD)和各向异性光谱的实验与计算方法
RSC Adv. 2021 Jan 5;11(3):1635-1643. doi: 10.1039/d0ra06832b. eCollection 2021 Jan 4.
2
Stereoselective biotransformation of racemic mandelic acid using immobilized laccase and (S)-mandelate dehydrogenase.使用固定化漆酶和(S)-扁桃酸脱氢酶对外消旋扁桃酸进行立体选择性生物转化。
Bioresour Bioprocess. 2017;4(1):2. doi: 10.1186/s40643-016-0135-3. Epub 2017 Jan 3.
3
Rationally re-designed mutation of NAD-independent L-lactate dehydrogenase: high optical resolution of racemic mandelic acid by the engineered Escherichia coli.
理性设计的 NAD 非依赖型 L-乳酸脱氢酶突变体:工程大肠杆菌对消旋扁桃酸的高光学分辨率。
Microb Cell Fact. 2012 Nov 23;11:151. doi: 10.1186/1475-2859-11-151.
4
Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid.大肠杆菌中 L-苯丙氨酸途径的代谢工程化生产 S-或 R-扁桃酸。
Microb Cell Fact. 2011 Sep 13;10:71. doi: 10.1186/1475-2859-10-71.
5
Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401.利用嗜粪产碱杆菌 ECU0401 的溴化十六烷基三甲铵透性化细胞对消旋扁桃腈进行生物催化合成(R)-(-)-扁桃酸。
J Ind Microbiol Biotechnol. 2010 Jul;37(7):741-50. doi: 10.1007/s10295-010-0720-y. Epub 2010 Apr 22.