酶法转化生产α-酮酸的研究进展
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摘要
α-酮酸是一种同时含有羧基和酮基的双官能团有机化合物,广泛应用于食品、药品和化妆品等行业。为了满足环境友好、安全高效和可持续发展的社会要求,利用酶转化法生产α-酮酸受到人们的广泛关注。文中从酶的筛选、酶的改造以及酶的转化条件优化3个方面介绍丙酮酸、α-酮戊二酸、酮亮氨酸、酮缬氨酸、苯丙酮酸和酮蛋氨酸酶法合成的研究状况,并展望了α-酮酸进一步高效生产的发展方向。
Alpha-keto acid is a bifunctional organic compound containing both carboxyl and ketone groups,and widely applied in the industries of food,pharmaceutical and cosmetics.Based on the demand of eco-friendly process,safety and sustainable development,production of a-keto acids by enzymatic conversion technology has been paid more and more attention.In this article,we review the status of a-keto acids biosynthesis from three aspects:enzymatic screening,enzymatic modification and optimization of enzymatic conversion conditions.Meanwhile,we also indicate future research directions for further improving a-keto acids production.
Alpha-keto acid is a bifunctional organic compound containing both carboxyl and ketone groups,and widely applied in the industries of food,pharmaceutical and cosmetics.Based on the demand of eco-friendly process,safety and sustainable development,production of a-keto acids by enzymatic conversion technology has been paid more and more attention.In this article,we review the status of a-keto acids biosynthesis from three aspects:enzymatic screening,enzymatic modification and optimization of enzymatic conversion conditions.Meanwhile,we also indicate future research directions for further improving a-keto acids production.
引文
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[33]Duncan PA,White BA,Mackie RI.Purification and properties of NADP-dependent glutamate dehydrogenase from Ruminococcus flavefaciens FD-1.Appl Environ Microbiol,1992,58(12):4032-4037.
[34]Zhang KX,Liu YS.Studies on glutamate dehydrogenase from Brevibacterium Tianjinese T6-13.Acta Microbiol Sin,1991,31(4):281-286(in Chinese).张克旭,刘永生.天津短杆菌T6-13谷氨酸脱氢酶的研究.微生物学报,1991,31(4):281-286.
[35]B?hmer A,Müller A,Passarge M,et al.A novel L-glutamate oxidase from Streptomyces endus purification and properties.Eur J Biochem,1989,182(2):327-332.
[36]Wachiratianchai S,Bhumiratana A,Udomsopagit S.Isolation,purification,and characterization of L-glutamate oxidase from Streptomyces sp.18G.Electron J Biotechnol,2004,7(3):274-281.
[37]Kusakabe H,Midorikawa Y,Kuninaka A,et al.Occurrence of a new enzyme,L-glutamate oxidase in a wheat bran culture extract of Streptomyces sp.X-119-6.Agricul Biol Chem,1983,47(1):175-177.
[38]Arima J,Sasaki C,Sakaguchi C,et al.Structural characterization of L-glutamate oxidase from Streptomyces sp.X‐119‐6.FEBS J,2010,276(14):3894-3903.
[39]Niu PQ,Zhang ZY,Liu LM.Enzymatic production ofα-ketoglutaric acid by L-glutamate oxidase from L-glutamic acid.Chin J Biotech,2014,30(8):1318-1322(in Chinese).牛盼清,张震宇,刘立明.酶法转化L-谷氨酸生产α-酮戊二酸.生物工程学报,2014,30(8):1318-1322.
[40]Motta P,Molla G,Pollegioni L,et al.Structure-function relationships in L-amino acid deaminase,a flavoprotein belonging to a novel class of biotechnologically relevant enzymes.J Biol Chem,2016,291(20):10457-10475.
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[2]Bückle-Vallant V,Krause FS,Messerschmidt S,et al.Metabolic engineering of Corynebacterium glutamicum for 2-ketoisocaproate production.Appl Microbiol Biotechnol,2014,98(1):297-311.
[3]Vogt M,Haas S,Polen T,et al.Production of2-ketoisocaproate with Corynebacterium glutamicum strains devoid of plasmids and heterologous genes.Microb Biotechnol,2015,8(2):351-360.
[4]Hossain GS,Shin HD,Li JH,et al.Transporter engineering and enzyme evolution for pyruvate production from D/L-alanine with a whole-cell biocatalyst expressing L-amino acid deaminase from Proteus mirabilis.RSC Adv,2016,6(86):82676-82684.
[5]Liu L,Hossain GS,Shin HD,et al.One-step production ofα-ketoglutaric acid from glutamic acid with an engineered L-amino acid deaminase from Proteus mirabilis.J Biotechnol,2013,164(1):97-104.
[6]Hossain GS,Li JH,Shin HD,et al.Bioconversion of L-glutamic acid toα-ketoglutaric acid by an immobilized whole-cell biocatalyst expressing L-amino acid deaminase from Proteus mirabilis.J Biotechnol,2014,169:112-120.
[7]Hossain GS,Li JH,Shin HD,et al.Improved production ofα-ketoglutaric acid(α-KG)by a Bacillus subtilis whole-cell biocatalyst via engineering of L-amino acid deaminase and deletion of theα-KG utilization pathway.J Biotechnol,2014,187:71-77.
[8]Niu PQ,Dong XX,Wang YC,et al.Enzymatic production ofα-ketoglutaric acid from L-glutamic acid via L-glutamate oxidase.J Biotechnol,2014,179:56-62.
[9]Fan XC,Chen RD,Chen LL,et al.Enhancement of alpha-ketoglutaric acid production from L-glutamic acid by high-cell-density cultivation.J Mol Catal B:Enzym,2016,126:10-17.
[10]Wu J,Fan XC,Liu J,et al.Promoter engineering of cascade biocatalysis forα-ketoglutaric acid production by coexpressing L-glutamate oxidase and catalase.Appl Microbiol Biotechnol,2018,102(11):4755-4764.
[11]Zhu YH,Li JH,Liu L,et al.Production ofα-ketoisocaproate via free-whole-cell biotransformation by Rhodococcus opacus DSM 43250 with L-leucine as the substrate.Enzyme Microb Technol,2011,49(4):321-325.
[12]Liu LM,Yuan YX,Liu J,et al.Method for efficiently producingα-ketoisocaproic by enzyme:CN,CN108587993A.2018-09-28(in Chinese).刘立明,袁宇翔,刘佳,等.一种酶法催化高产α-酮异己酸的方法:CN,CN108587993A.2018-09-28.
[13]Liu LM,Yuan YX,Chen XL,et al.A method for constructing L-amino acid deaminase mutant and its application:CN,CN108624576A.2018-10-09(in Chinese).刘立明,袁宇翔,陈修来,等.一种L-氨基酸脱氨酶的突变体及其制备方法与应用:CN,CN108624576A.2018-10-09.
[14]Song Y,Li JH,Shin H,et al.Tuning the transcription and translation of L-amino acid deaminase in Escherichia coli improvesα-ketoisocaproate production from L-leucine.PLoS ONE,2017,12(6):e0179229.
[15]Li RX,Sakir HG,Li JH,et al.Rational molecular engineering of L-amino acid deaminase for production ofα-ketoisovaleric acid from L-valine by Escherichia coli.RSC Adv,2017,7(11):6615-6621.
[16]Wu J,Pei SS,Liu J,et al.Method for efficiently producingα-ketoisocaproate:CN,201811350903.7.2018-11-20(in Chinese).吴静,裴杉杉,刘佳,等.一种高产α-酮异戊酸的方法:CN,201811350903.7.2018-11-20.
[17]Wu J,Pei SS,Liu J,et al.A method for constructing L-amino acid oxidase mutant:CN,201811350819.5.2018-11-20(in Chinese).吴静,裴杉杉,刘佳,等.一种L-氨基酸氧化酶的突变体:CN,201811350819.5.2018-11-20.
[18]Liu J,Wu J,Yang B,et al.Method for efficiently producing phenylpyruvic acid:CN,CN108841844A.2018-11-20(in Chinese).刘佳,吴静,杨彬,等.一种高效生产苯丙酮酸的方法:CN,CN108841844A.2018-11-20.
[19]Liu J,Wu J,Yang B,et al.A method for production of phenylpyruvic acid by enzyme bioconversion:CN,CN109022338A.2018-12-18(in Chinese).刘佳,吴静,杨彬,等.一种酶转化苯丙氨酸生产苯丙酮酸的工艺:CN,CN109022338A.2018-12-18.
[20]Liu LM,Zhang C,Liu J,et al.Method for efficiently producing KMTB(alpha-keto-gamma-methylthiobutyric acid):CN,CN107988131A.2018-05-04(in Chinese).刘立明,张灿,刘佳,等.一种高产α-酮-γ-甲硫基丁酸的方法:CN,CN107988131A.2018-05-04.
[21]Liu LM,Li Y,Du GC,et al.Progress in biotechnological production of pyruvic acid.Chin J Biotech,2002,18(6):651-655(in Chinese).刘立明,李寅,堵国成,等.生物技术法生产丙酮酸的研究进展.生物工程学报,2002,18(6):651-655.
[22]Gu JS,Xu P,Li TL,et al.Preparation of pyruvate from lactateby lactate oxidase.Chin J Appl Environ Biol,2001,7(6):617-620(in Chinese).谷劲松,许平,李铁林,等.乳酸氧化酶转化乳酸产丙酮酸.应用与环境生物学报,2001,7(6):617-620.
[23]Mu WM,Yu SH,Jiang B,et al.Characterization of D-lactate dehydrogenase from Pediococcus acidilactici that converts phenylpyruvic acid into phenyllactic acid.Biotechnol Lett,2012,34(5):907-911.
[24]Zhao T.Cloning,overexpression and properties of ldh gene from Lactobacillus paracasei[D].Suzhou:Soochow University,2012(in Chinese).赵婷.副干酪乳杆菌乳酸脱氢酶的克隆表达及酶学性质的研究[D].苏州:苏州大学,2012.
[25]Eisenberg A,Seip JE,Gavagan JE,et al.Pyruvic acid production using methylotrophic yeast transformants as catalyst.J Mol Catal B:Enzym,1997,2(4/5):223-232.
[26]Chowdhury EK,Saitoh T,Nagata S,et al.Alanine dehydrogenase from Enterobacter aerogenes:purification,characterization,and primary structure.Biosci Biotechnol Biochem,1998,62(12):2357-2363.
[27]Molla G,Melis R,Pollegioni L.Breaking the mirror:L-amino acid deaminase,a novel stereoselective biocatalyst.Biotechnol Adv,2017,35(6):657-668.
[28]Pollegioni L,Motta P,Molla G.L-amino acid oxidase as biocatalyst:a dream too far?Appl Microbiol Biotechnol,2013,97(21):9323-9341.
[29]ButòS,Pollegioni L,D'Angiuro L,et al.Evaluation of D-amino acid oxidase from Rhodotorula gracilis for the production ofα-keto acids:a reactor system.Biotechnol Bioeng,1994,44(11):1288-1294.
[30]Hao JR,Ma CQ,Gao C,et al.Pseudomonas stutzeri as a novel biocatalyst for pyruvate production from DL-lactate.Biotechnol Lett,2007,29(1):105-110.
[31]Chernyavskaya OG,Shishkanova NV,Il’Chenko AP,et al.Synthesis ofα-ketoglutaric acid by Yarrowia lipolytica yeast grown on ethanol.Appl Microbiol Biotechnol,2000,53(2):152-158.
[32]Yang SH,Tan LL,Liao M,et al.Effects ofα-ketoglutarate on growth performance and meat quality of broilers under heat stress.Feed Ind Mag,2014,35(22):11-16(in Chinese).杨书慧,谭灵琳,廖满,等.α-酮戊二酸对热应激肉鸡生长性能和肌肉品质的影响.饲料工业,2014,35(22):11-16.
[33]Duncan PA,White BA,Mackie RI.Purification and properties of NADP-dependent glutamate dehydrogenase from Ruminococcus flavefaciens FD-1.Appl Environ Microbiol,1992,58(12):4032-4037.
[34]Zhang KX,Liu YS.Studies on glutamate dehydrogenase from Brevibacterium Tianjinese T6-13.Acta Microbiol Sin,1991,31(4):281-286(in Chinese).张克旭,刘永生.天津短杆菌T6-13谷氨酸脱氢酶的研究.微生物学报,1991,31(4):281-286.
[35]B?hmer A,Müller A,Passarge M,et al.A novel L-glutamate oxidase from Streptomyces endus purification and properties.Eur J Biochem,1989,182(2):327-332.
[36]Wachiratianchai S,Bhumiratana A,Udomsopagit S.Isolation,purification,and characterization of L-glutamate oxidase from Streptomyces sp.18G.Electron J Biotechnol,2004,7(3):274-281.
[37]Kusakabe H,Midorikawa Y,Kuninaka A,et al.Occurrence of a new enzyme,L-glutamate oxidase in a wheat bran culture extract of Streptomyces sp.X-119-6.Agricul Biol Chem,1983,47(1):175-177.
[38]Arima J,Sasaki C,Sakaguchi C,et al.Structural characterization of L-glutamate oxidase from Streptomyces sp.X‐119‐6.FEBS J,2010,276(14):3894-3903.
[39]Niu PQ,Zhang ZY,Liu LM.Enzymatic production ofα-ketoglutaric acid by L-glutamate oxidase from L-glutamic acid.Chin J Biotech,2014,30(8):1318-1322(in Chinese).牛盼清,张震宇,刘立明.酶法转化L-谷氨酸生产α-酮戊二酸.生物工程学报,2014,30(8):1318-1322.
[40]Motta P,Molla G,Pollegioni L,et al.Structure-function relationships in L-amino acid deaminase,a flavoprotein belonging to a novel class of biotechnologically relevant enzymes.J Biol Chem,2016,291(20):10457-10475.
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