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生物法合成4-羟基异亮氨酸的代谢工程研究进展

  • 李洋 ,
  • 张稳杰 ,
  • 韩雨辰 ,
  • 翟懿雪 ,
  • 张成林
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  • (天津科技大学 生物工程学院,天津,300457)
本科生(张成林副教授为通信作者, E-mail: zcl@tust.edu.cn)

网络出版日期: 2022-04-06

基金资助

国家自然科学基金项目(32170049, 31300069);天津市高等学校大学生创新训练计划项目(202010057030);中国博士后科学基金项目(2017M611170, 2018T110662)

Advances on metabolic engineering for biosynthesis of 4-hydroxyisoleucine

  • LI Yang ,
  • ZHANG Wenjie ,
  • HAN Yuchen ,
  • ZHIA Yixue ,
  • ZHANG Chenglin
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  • (College of Biotechnology,Tianjin University of Science and Technology,Tianjin 300457,China)

Online published: 2022-04-06

摘要

4-羟基异亮氨酸是一种非蛋白质氨基酸,因具有血糖浓度依赖的诱导胰岛素分泌等生物学活性,而被视为治疗糖尿病的潜在药物。近年来,生物法合成4-羟基异亮氨酸取得了一定的进展。文章概述了4-羟基异亮氨酸的功能、合成方法及其生物合成途径。在此基础上,从构建4-异亮氨酸合成途径、强化L-异亮氨酸合成、重构中心代谢途径等层面着重阐述了生物法合成4-羟基异亮氨酸的代谢工程策略,旨在为以4-羟基异亮氨酸为代表的高附加值氨基酸衍生物合成菌株代谢工程研究提供参考。

本文引用格式

李洋 , 张稳杰 , 韩雨辰 , 翟懿雪 , 张成林 . 生物法合成4-羟基异亮氨酸的代谢工程研究进展[J]. 食品与发酵工业, 2022 , 48(5) : 281 -288 . DOI: 10.13995/j.cnki.11-1802/ts.028005

Abstract

4-Hydroxyisoleucine,a non-protein amino acid,has been considered as a potential alternative for diabetes-curing drugs.In recent years,considerable progress has been made on biosynthesis of 4-hydroxyisoleucine.In this study,the function,synthesis methods as well as biosynthesis pathway of 4-hydroxyisoleucine are illustrated.Furthermore,the metabolic engineering strategies are summarized,including construction of 4-hydroxyisoleucine biosynthesis pathway,enhancement of L-isoleucine synthesis and reconstruction of central pathways.It aims to provide a reference for metabolic engineering strains for producing value-added amino acid derivatives.

参考文献

[1] FOWDEN L,PRATT H M,SMITH A,et al.4-Hydroxyisoleucine from seeds of Trigonella foenum-graecum[J].Phytochemistry,1973,12(7):1 707-1 711.
[2] AHMAD A,ALGHAMDI SS,MAHMOOD K,et al.Fenugreek a multipurpose crop:potentialities and improvements[J].Saudi Journal of Biological Sciences,2016,23(2):300-310.
[3] MOHAMMAD-SADEGHIPOUR M,MAHMOODI M,KARIMABAD M N,et al.Diosgenin and 4-hydroxyisoleucine from fenugreek are regulators of genes involved in lipid metabolism in the human colorectal cancer cell line SW480[J].Cell Journal,2021,22(4):514-522.
[4] YANG J L,RAN Y H,YANG Y H,et al.4-Hydroxyisoleucine alleviates macrophage-related chronic inflammation and metabolic syndrome in mice fed a high-fat diet[J].Frontiers in Pharmacology,2021,11:606514.
[5] ZAFAR M I,GAO F.4-Hydroxyisoleucine:A potential new treatment for type 2 diabetes mellitus[J].BioDrugs:Clinical Immunotherapeutics,Biopharmaceuticals,2016,30(4):255-262.
[6] SAUVAIRE Y,PETIT P,BROCA C,et al.4-Hydroxyisoleucine,a novel amino acid potentiator of insulin secretion[J].Diabetes,1998,47(2):206-210.
[7] MASIELLO P,BROCA C,GROSS R,et al.Experimental NIDDM development of a new model in adult rats administered Streptozotocin and nicotinamide[J].Diabetes,1998,47(2):224-229.
[8] MAURYA C K,SINGH R,JAISWAL N,et al.4-Hydroxyisoleucine ameliorates fatty acid-induced insulin resistance and inflammatory response in skeletal muscle cells[J].Molecular & Cellsular Endocrinology,2014,395(1):51-60.
[9] SHARMA R D,RAGHURAM T C,RAO N S.Effect of fenugreek seeds on blood glucose and serum lipids in type I diabetes[J].European Journal of Clinical Nutrition,1990,44(4):301-306.
[10] GALINSKI E A,PFEIFFER H P,TRUPER H G.1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid[J].European Journal of Biochemistry,1985,149(1):135-139.
[11] SAUVAIRE Y,GIRARDON P,BACCOU J C,et al.Changes in growth,proteins and free amino acids of developing seed and pod of fenugreek[J].Phytochemistry,1984,23(3):479-486.
[12] 李玉山.胡芦巴中4-羟基异亮氨酸的提取分离工艺研究[J].食品科学,2009,30(8):128-131.
LI Y S.Study on extraction and purification of 4-hydroxyisoleucine from Trigonella foenungraecum[J].Food Science,2009,30(8):128-131.
[13] BEN-ISHAI D,BERLER Z,ALTMAN J,et al.A new synthesis of α-amino acids.Amidoalkylation of active methylene compounds with glyoxylic acid derivatives[J].Journal of the Chemical Society Chemical Communications,1975,7(22):905-906.
[14] GULL R,SCHLLKOPF U.Asymmetric Syntheses via Heterocyclic Intermediates;XXVII1.Enantioselective synthesis of[2-methoxyethoxymethyl-protected](R)-homoserine methyl esters and (R)-α-methyl-homoserine methyl esters and of the corresponding α-amino-γ-lactones by the bis-lactim ether method[J].Synthesis,1985,1985(11):1 052-1 055.
[15] INGHARDT T,FREJD T,SVENSSON G.Organoaluminium induced ring opening of epoxypyranosides.IV.Synthesis and structure of γ-hydroxylsoleucine stereoisomers and their corresponding lactones[J].Tetrahedron,1991,47(32):6 469-6 482.
[16] 陈平,吴成龙,邓勇.(2S,3R,4S)-4-羟基异亮氨酸的不对称合成[J].中国医药工业杂志,2010,41(7):491-494.
CHEN P,WU C L,DENG Y.Asymmetric synthesis of(2S,3R,4S)-4-hydroxyisoleucine[J].Chinese Journal of Pharmaceuticals 2010,41(7):491-494.
[17] WANG Q,OUAZZANI J,SASAKI N A,et al.A practical synthesis of(2S,3R,4S)-4-hydroxyisoleucine,a potent insulinotropic α-amino acid from fenugreek[J].European Journal of Organic Chemistry,2002,5(1):834-839.
[18] FULCRAND V R,ROLLAND M,ROUMESTANT M L,et al.Chemoenzymatic synthesis of enantiomerically pure(2S,3R,4S)-4-hydroxyisoleucine,an insulinotropic amino acid isolated from fenugreek seeds[J].European Journal of Organic Chemistry,2004,2004(4):873-877.
[19] SMIRNOV S V,SAMSONOVA N N,NOVIKOVA A E,et al.A novel strategy for enzymatic synthesis of 4-hydroxyisoleucine:identification of an enzyme possessing HMKP(4-hydroxy-3-methyl-2-keto-pentanoate) aldolase activity[J].FEMS Microbiology Letters,2007,273(1):70-77.
[20] SHI X,MIYAKAWA T,NAKAMURA A,et al.Engineering a short-chain dehydrogenase/reductase for the stereoselective production of(2S,3R,4S)-4-hydroxyisoleucine with three asymmetric centers[J].Scientific Reports,2017,7:73703.
[21] HAEFEL C,BONFILS C,SAUVAIRE Y.Characterization of a dioxygenase from Trigonella foenum-graecum involved in 4-hydroxyisoleucine biosynthesis[J].Phytochemistry,1997,44(4):563-566.
[22] KODERA T,SMIRNOV S V,SAMSONOVA N N,et al.A novel L-isoleucine hydroxylating enzyme,L-isoleucine dioxygenase from Bacillus thuringiensis,produces(2S,3R,4S)-4-hydroxyisoleucine[J].Biochemical & Biophysical Research Communications,2009,390(3):506-510.
[23] KIVERO A D,NOVIKOVA A E,SMIRNOV S V.Modification of E.coli central metabolism to optimize the biotransformation of L-isoleucine into 4-hydroxyisoleucine by enzymatic hydroxylation[J].Applied Biochemistry and Microbiology,2012,48(7):639-644.
[24] SHI F,NIU T F,FANG H M.4-Hydroxyisoleucine production of recombinant Corynebacterium glutamicum ssp.lactofermentum under optimal corn steep liquor limitation[J].Applied microbiology and biotechnology,2015,99(9):3 851-3 863.
[25] SHI F,FANG H M,NIU T F,et al.Overexpression of ppc and lysC to improve the production of 4-hydroxyisoleucine and its precursor L-isoleucine in recombinant Corynebacterium glutamicum ssp.lactofermentum[J].Enzyme and Microbial Technology,2016,87-88:79-85.
[26] SHI F,ZHANG M L,LI Y F,et al.Sufficient NADPH supply and pknG deletion improve 4-hydroxyisoleucine production in recombinant Corynebacterium glutamicum[J].Enzyme and Microbial Technology,2018,115:1-8.
[27] 张成林,刘远,薛宁,等.苏云金芽孢杆菌重组L-异亮氨酸羟化酶的酶学性质及其在4-羟基异亮氨酸合成中的应用[J].微生物学报,2014,54(8):889-896.
ZHANG C L,LIU Y,XUE N,et al.Characterization of recombinant L-isoleucine-4-hydroxylase from Bacillus thuringiensis and its application in 4-hydroxyisoleucine biosynthesis[J].Acta Microbiologica Sinica,2014,54(8):889-896.
[28] ZHANG C L,MA J,LI Z X,et al.A strategy for L-isoleucine dioxygenase screening and 4-hydroxyisoleucine production by resting cells[J].Bioengineered,2018,9(1):72-79.
[29] 李英滋,张宇,王道安,等.合成4-羟基异亮氨酸的大肠杆菌构建及其催化体系优化[J].天津科技大学学报,2020,35(3):9-15.
LI Y Z,ZHANG Y,WANG D A,et al.Construction of Escherich coli strain for 4-hydroxyisoleucine biosynthesis and optimization of its biocatalyzing system[J].Journal of Tianjin University of Science & Technology,2020,35(3):9-15.
[30] DU P,YAN S,QIAN X L,et al.Engineering Bacillus subtilis isoleucine dioxygenase for efficient synthesis of(2S,3R,4S)-4-Hydroxyisoleucine[J].Journal of Agricultural and Food Chemistry,2020,68(49):14 555-14 563.
[31] TAN S Y,SHI F,LIU H Y,et al.Dynamic control of 4-hydroxyisoleucine biosynthesis by modified L-isoleucine biosensor in recombinant Corynebacterium glutamicum[J].ACS Synthetic Biology,2020,9(9):2 378-2 389.
[32] ZHANG C L,LI Y J,MA J,et al.High production of 4-hydroxyisoleucine in Corynebacterium glutamicum by multistep metabolic engineering[J].Metabolic Engineering,2018,49:287-298.
[33] OGAWA J,KODERA T,SMIRNOV S V,et al.A novel L-isoleucine metabolism in Bacillus thuringiensis generating(2S,3R,4S)-4-hydroxyisoleucine,a potential insulinotropic and anti-obesity amino acid[J].Applied Microbiology and Biotechnology,2011,89(6):1 929-1 938.
[34] 朱福周,董解荣,陈宁,等.生物法合成α-酮戊二酸及其衍生物的研究进展[J].中国酿造,2020,39(3):1-6.
ZHU F Z,DONG J R,CHEN N,et al.Research progress in biosynthesis of α-ketoglutarate and its derivatives[J].China Brewing,2020,49(3):287-298.
[35] YAMAMOTO K,TSUCHISAKA A,YUKAWA H.Branched-chain amino acids[J].Advances in Biochemical Engineer Biotechnology,2017,159:103-128.
[36] 芦楠,李宇虹,陈宁,等.L-异亮氨酸及其衍生物代谢工程研究进展[J].食品与发酵工业,2021,47(9):307-313.
LU N,LI Y H,CHEN N,et al.Advances on metabolic engineering of L-isoleucine and its derivatives[J].Food and Fermentation Industries,2021,47(9):307-313.
[37] 卢正珂,史锋.过表达mqo对重组谷氨酸棒杆菌L-异亮氨酸和4-羟基异亮氨酸合成的影响[J].食品与发酵工业,2017,43(10):30-35.
LU Z K,SHI F.Effects of mqo overexpression on the synthesis of L-isoleucine and 4-hydroxyisoleucine in recombinant Corynebacterium glutamicum[J].Food and Fermentation Industries,2017,43(10):30-35.
[38] SHI F,ZHANG S P,LI Y F,et al.Enhancement of substrate supply and ido expression to improve 4-hydroxyisoleucine production in recombinant Corynebacterium glutamicum ssp.lactofermentum[J].Applied Microbiology and Biotechnology,2019,103(10):4 113-4 124.
[39] SHI F,FAN Z Y,ZHANG S P,et al.Optimization of ribosomal binding site sequences for gene expression and 4-hydroxyisoleucine biosynthesis in recombinant Corynebacterium glutamicum[J].Enzyme and Microbial Technology,2020,140:109622.
[40] OGAWA J,KODERA T,SMIRNOV K S,et al.A novelL-isoleucine metabolism in Bacillus thuringiensis generating (2S,3R,4S)-4-hydroxyisoleucine,a potential insulinotropic and anti-obesity amino acid[J].Applied Microbiology and Biotechnology,2011,89:1 929-1 938.
[41] KIVERO A D,BOCHAROV E V,DOROSHENKO V G,et al.2D[1H,13C] NMR study of carbon fluxes during glucose utilization by Escherichia coli MG1655[J].Applied Microbiology and Biotechnology,2008,44(2):168-175.
[42] NIEBISCH A,KABUS A,SCHULTZ C,et al.Corynebacterial protein kinase G controls 2-oxoglutarate dehydrogenase activity via the phosphorylation status of the OdhI protein[J].Journal of Biological Chemistry,2006,281(18):12 300-12 307.
[43] LANGE C,MUSTAFI N,FRUNZKE J,et al.Lrp of Corynebacterium glutamicum controls expression of the brnFE operon encoding the export system for L-methionine and branched-chain amino acids[J].Journal of Biotechnology,2012,158(4):231-241.
[44] MORBACH S,JUNGER C,SAHM H,et al.Attenuation control of ilvBNC in Corynebacterium glutamicum:Evidence of leader peptide formation without the presence of a ribosome binding site[J].Journal of Bioscience and Bioengineering,2000,90(5):501-507.
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