|本期目录/Table of Contents|

[1]李恩杰,汤晓玲,吴哲明,等.重组腈水解酶催化合成(S)-3-氰基-5-甲基己酸[J].生物加工过程,2019,17(01):99-103.[doi:10.3969/j.issn.1672-3678.2019.01.013]
 LI Enjie,TANG Xiaoling,WU Zheming,et al.Synthesis of(S)-3-cyano-5-methylhexanoic acid catalyzed by recombinant nitrilase[J].Chinese Journal of Bioprocess Engineering,2019,17(01):99-103.[doi:10.3969/j.issn.1672-3678.2019.01.013]
点击复制

重组腈水解酶催化合成(S)-3-氰基-5-甲基己酸()
分享到:

《生物加工过程》[ISSN:1672-3678/CN:32-1706/Q]

卷:
17
期数:
2019年01期
页码:
99-103
栏目:
出版日期:
2019-01-30

文章信息/Info

Title:
Synthesis of(S)-3-cyano-5-methylhexanoic acid catalyzed by recombinant nitrilase
文章编号:
1672-3678(2019)01-0099-05
作者:
李恩杰汤晓玲吴哲明郑仁朝
浙江工业大学 生物工程学院,浙江 杭州 310014
Author(s):
LI EnjieTANG XiaolingWU ZhemingZHENG Renchao
College of Biotechnology and Bioengineering,Zhejiang University of Technology,Hangzhou 310014,China
关键词:
普瑞巴林 腈水解酶 生物催化 异丁基丁二腈(S)-3-氰基-5-甲基己酸
分类号:
TQ46;O623.76
DOI:
10.3969/j.issn.1672-3678.2019.01.013
文献标志码:
A
摘要:
(S)-3-氰基-5-甲基己酸是合成普瑞巴林的关键手性中间体。笔者以表达来源于Brassica rapa subsp.的重组腈水解酶工程菌BrNit为催化剂,不对称水解外消旋异丁基丁二腈(IBSN)制备(S)-3-氰基-5-甲基己酸。考察反应温度、pH以及不同底物浓度和金属离子对全细胞催化IBSN水解的影响。结果表明:全细胞催化的最适温度为30 ℃,最适pH为8.0,最适底物浓度为180 mmol/L。在此条件下,利用10 g/L湿菌体催化水解IBSN,反应6 h转化率可达45.1%,产物对映体过量值(e.e.值)达到97.9%。

参考文献/References:

[1] PACE H C,BRENNER C.The nitrilase superfamily:classification,structure and function[J].Genome Biol,2001,2(1):1-9.
[2] MATHEW S,NADARAJAN S P,SUNDARAMOORTHY U,et al.Biotransformation of β-keto nitriles to chiral(S)-β-amino acids using nitrilase and ω-transaminase[J].Biotechnol Lett,2017,39(4):535-543.
[3] LUO H,MA J,CHANG Y,et al.Directed evolution and mutant characterization of nitrilase from Rhodococcus rhodochrous tg1-A6[J].Appl Biochem Biotechnol,2016,178(8):1510-1521.
[4] LEHMANN T,JANOWITZ T,S?NCHEZPARRA B,et al.Arabidopsis nitrilase 1 contributes to the regulation of root growth and development through modulation of auxin biosynthesis in seedlings[J].Front Plant Sci,2017,8:1-15.
[5] SINGH R,SHARMA R,TEWARI N,et al.Nitrilase and its application as a ’green’ catalyst[J].Chem Biodiv,2006,3(12):1279-1287.
[6] 徐建妙,郑裕国,沈寅初.腈水解酶的来源、结构、作用机制及其应用[J].微生物学通报,2005,32(5):141-146.
[7] 郑裕国,薛亚平,柳志强,等.腈转化酶在精细化学品生产中的应用[J].生物工程学报,2009,25(12):1795-1807.
[8] CHEN J,ZHENG R C,ZHENG Y G,et al.Microbial transformation of nitriles to high-value acids or amides[J].Adv Biochem Eng Biotechnol,2009,113(35):33-77.
[9] 何玉财,周琼,林春昕,等.一种腈水解酶的高通量筛选方法[J].高校化学工程学报,2012(5):853-857.
[10] 龚劲松,李恒,谢旻峰,等.重组真菌腈水解酶的发酵工艺条件及生物催化特性初探[J].精细化工,2015,32(10):1112-1118.
[11] 李继彬,陈志,陈华友.腈水解酶克隆表达、固定化及分子改造的研究进展[J].中国生物工程杂志,2017,37(9):141-147.
[12] 吴洋,薛亚平,郑裕国.金属螯合载体固定重组腈水解酶[J].生物加工过程,2012,10(4):47-53.
[13] SILVERMANN R B.ChemInform abstract:from basic science to blockbuster drug-the discovery of lyrica[J].Angew Chem Int Ed,2008,47(19):3500-3504.
[14] LEE C H,LIOU H H.Pregabalin activates ROMK1 channels via cAMP-dependent protein kinase and protein kinase C[J].Eur J Pharmacol,2014,740:35-44.
[15] 于玉振,张晓慧,李鹏坤,等.普瑞巴林晶型Ⅰ在纯溶剂及丙酮-水混合溶剂中的溶解度测定与关联[J].高校化学工程学报,2017,31(1):7-12.
[16] BELLIOTTI T R,CAPIRIS T,EKHATO I V,et al.Structure-activity relationships of pregabalin and analogues that target the alpha(2)-delta protein[J].J Med Chem,2005,48(7):2294-2307.
[17] 聂雅洁,郑仁朝,柳志强,等.拟南芥腈水解酶催化合成普瑞巴林中间体(S)-3-氰基-5-甲基己酸[J].精细与专用化学品,2014,22(5):19-23.
[18] MARTINEZ C A,HU S,DUMOND Y,et al.Development of a chemoenzymatic manufacturing process for pregabalin[J].Org Proc Res Developt,2008,12(3):392-398.
[19] XIE Z,FENG J,GARCIA E,et al.Cloning and optimization of a nitrilase for the synthesis of(3 S)-3-cyano-5-methyl hexanoic acid[J].J Mol Catal B Enzym,2006,41(3):75-80.
[20] ZHENG R C,LI A P,WU Z M,et al.Enzymatic production of(S)-3-cyano-5-methylhexanoic acid ethyl ester with high substrate loading by immobilized Pseudomonas cepacia lipase[J].Tetrahedron Asymmetry,2012,23(22-23):1517-1521.
[21] CHAUDHARI K,YEOLE M,BATCHU C,et al.A novel process for synthesis of pregabalin from substituted cyclopropane intermediate and a process for enzymatic resolution of racemic pregabalin:WO2009087650[P].2009-07-16.
[22] BANERJEE A,KAUL P,BANERJEE U C.Enhancing the catalytic potential of nitrilase from Pseudomonas putida for stereoselective nitrile hydrolysis[J].Appl Microb Biotechnol,2006,72(1):77-87.
[23] LIU Z Q,DONG L Z,CHENG F,et al.Gene cloning,expression,and characterization of a nitrilase from Alcaligenes faecalis ZJUTB10[J].J Agric Food Chem,2011,59(21):11560-11570.
[24] SOHONI S V,NELAPATI D,SATHE S,et al.Optimization of high cell density fermentation process for recombinant nitrilase production in E.coli[J].Bioresour Technol,2015,188:202-208.
[25] ZHANG Z J,XU J H,HE Y C,et al.Efficient production of(R)-(-)-mandelic acid with highly substrate/product tolerant and enantioselective nitrilase of recombinant Alcaligenes sp.[J].Proc Biochem,2010,45(6):887-891.
[26] ZHANG Z J,XU J H,HE Y C,et al.Cloning and biochemical properties of a highly thermostable and enantioselective nitrilase from Alcaligenes sp.ECU0401 and its potential for(R)-(-)-mandelic acid production[J].Bioproc Biosyst Eng,2011,34(3):315-322.
[27] DESANTIS G,WONG K,FARWELL B,et al.Creation of a productive,highly enantioselective nitrilase through gene site saturation mutagenesis(GSSM)[J].J Am Chem Soc,2003,125(38):11476-11477.

相似文献/References:

[1]吴洋,薛亚平,郑裕国.金属螯合载体固定重组腈水解酶[J].生物加工过程,2012,10(04):47.[doi:10.3969/j.issn.1672-3678.2012.04.011]
 WU Yang,XUE Yaping,ZHENG Yuguo.Immobilization of recombinant nitrilase on metal chelating carriers[J].Chinese Journal of Bioprocess Engineering,2012,10(01):47.[doi:10.3969/j.issn.1672-3678.2012.04.011]
[2]汤晓芒,张鲁嘉,崔东冰,等.通过分析来自Pyrococcus abyssi的腈水解酶中带电基团位置变化探讨蛋白耐热机制[J].生物加工过程,2012,10(06):29.[doi:10.3969/j.issn.1672-3678.2012.06.006]
 TANG Xiaomang,ZHANG Lujia,CUI Dongbing,et al.Mechanism of protein thermostability by analyzing change of ionizable group position in nitrilase from Pyrococcus abyssi[J].Chinese Journal of Bioprocess Engineering,2012,10(01):29.[doi:10.3969/j.issn.1672-3678.2012.06.006]

备注/Memo

备注/Memo:
收稿日期:2018-05-06修回日期:2018-05-15
基金项目:浙江省自然科学杰出青年基金(LR19B060001)
作者简介:李恩杰(1991—),男,河南中牟人,硕士研究生,研究方向:生物催化; 郑仁朝(联系人),教授,E-mail:zhengrc@zjut.edu.cn
引文格式:李恩杰,汤晓玲,吴哲明,等.重组腈水解酶催化合成(S)-3-氰基-5-甲基己酸[J].生物加工过程,2019,17(1):99-103.
LI Enjie,TANG Xiaoling,WU Zheming,et al.Synthesis of(S)-3-cyano-5-methylhexanoic acid catalyzed by recombinant nitrilase[J].Chin J Bioprocess Eng,2019,17(1):99-103..
更新日期/Last Update: 2019-01-30