L-苯丙氨酸制备的研究进展
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摘要
笔者对化学和生物合成L-苯丙氨酸的研究进展进行了综述。首先简述L-苯丙氨酸化学合成和酶促合成方法;然后综述微生物发酵法制备L-苯丙氨酸的研究进展,简单介绍大肠杆菌和谷氨酸棒杆菌发酵法生成L-苯丙氨酸的代谢机制,同时,对发酵法合成L-苯丙氨酸的各项应用研究展开重点介绍;最后,对L-苯丙氨酸在生物领域的发展进行了展望。
Research progress on chemical and microbial synthesis of L-phenylalanine was reviewed.First,the chemical synthesis routes and enzymatic methods were discussed.Then,advances of the biosynthesis of phenylalanine via microbial fermentation were summarized,and the catalytic mechanisms of Escherichia coli and Corynebacterium glutamicum were also briefly discussed.The applications of L-phenylalanine biosynthesis were emphatically introduced.Finally,future research and applications of L-phenylalanine in biotechnology areas were also discussed.
Research progress on chemical and microbial synthesis of L-phenylalanine was reviewed.First,the chemical synthesis routes and enzymatic methods were discussed.Then,advances of the biosynthesis of phenylalanine via microbial fermentation were summarized,and the catalytic mechanisms of Escherichia coli and Corynebacterium glutamicum were also briefly discussed.The applications of L-phenylalanine biosynthesis were emphatically introduced.Finally,future research and applications of L-phenylalanine in biotechnology areas were also discussed.
引文
[1] 邓菊香,王祖元.苯丙氨酸的生产现状与发展前景[J].安徽化工,2007,33(4):1-3.
[2] RODRIGUEZ A,MARTNEZ J A,FLORES N,et al.Engineering Escherichia coli to overproduce aromatic amino acids and derived compounds[J].Microb Cell Fact,2014,13(1):126.
[3] 汪多仁.L-苯丙氨酸生产与应用[J].发酵科技通讯,2011,40(1):29-36.
[4] BONGAERTS J,KR?MER M,MüLLER U,et al.Metabolic engineering for microbial production of aromatic amino acids and derived compounds[J].Metab Eng,2001,3(4):289-300.
[5] DANIALI G,JINAP S,SANNY M,et al.Effect of amino acids and frequency of reuse frying oils at different temperature on acrylamide formation in palm olein and soy bean oils via modeling system[J].Food Chem,2018,245:1-6.
[6] 何若平,周华,韦萍.L-苯丙氨酸的生产及市场分析[J].精细石油化工进展,2000,12(1):47-49.
[7] 冷崇姣.L-苯丙氨酸的制备与应用前景[J].重庆科技学院学报(社会科学版),2004,19(4):9-11.
[8] TACHIBANA Y,ANDO M,KUZUHARA H.Asymmetric synthesis of α-amino acids by nonenzymatic transamination[J].J Syn Org,1983,42(2):134-142.
[9] 洪泽湖.苯丙氨酸制备技术的进展[J].湖南化工,1997,27(4):11-14.
[10] 齐欣,赵温涛,聂建明,等.DL-苯丙氨酸合成新方法[J].化学工业与工程,2002,19(5):394-397.
[11] OJIMA I,YODA N.N-carbamoyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidines(CAPP):efficient new chiralligands for asymmetric hydrogenation[J].Tetrahedron Lett,1980,21(11):1051-1054.
[12] LIN S H,CHEN C N,JUANG R S.Extraction equilibria and separation of phenylalanine and aspartic acid from water with di(2-ethylhexyl)phosphoric acid[J].J Chem Technol Biotechnol,2006,81(3):406-412.
[13] MENG C C,SHENG Y J,CHEN Q B,et al.Exceptional chiral separation of amino acid modified graphene oxide membranes with high-flux[J].J Membr Sci,2017,526:25-31.
[14] WU H,ZHAO Y Y,N M C,et al.Molecularly imprinted organic-inorganic hybrid membranes for selective separation of phenylalanine isomers and its analogue[J].Sep Purif Technol,2009,68(1):97-104.
[15] ZHANG Z,ZHANG M,LIU Y,et al.Preparation of L-phenylalanine imprinted polymer based on monodisperse hybrid silica microsphere and its application on chiral separation of phenylalanine racemates as HPLC stationary phase[J].Sep Purif Technol,2012,87(10):142-148.
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[33] LIU Y,LI P,ZHAO K B,et al.Corynebacterium glutamicum contains 3-deoxy-D-arabino-heptulosonate 7-phosphate synthases that display novel biochemical features[J].Appl Environ Microbiol,2008,74(17):5497-5503.
[34] LI P P,LI D F,LIU D,et al.Interaction between DAHP synthase and chorismate mutase endows new regulation on DAHP synthase activity in Corynebacterium glutamicum[J].Appl Environ Microbiol,2013,97(24):10373-10380.
[35] LI P P,LIU Y J,LIU S J.Genetic and biochemical identification of the chorismate mutase from Corynebacterium glutamicum[J].Microbiology,2009,155(10):3382-3391.
[36] EGGELING L,BOTT M.Handbook of Corynebacterium glutamicum[M].Boca Raton:CRC Press,2005.
[37] HATAI S.Mutational analysis of feedback inhibition and catalytic sites of prephenate dehydratase from Corynebacterium glutamicum[J].Arch Microbiol,2004,181(3):237-244.
[38] ZHANG S,WILSON D B,GANEM B.Probing the catalytic mechanism of prephenate dehydratase by site-directed mutagenesis of the Escherichia coli P-protein dehydratase domain[J].Biochemistry,2000,39(16):4722-4728.
[39] CHAN M S,HSU W H.Cloning of m-fluorophenylalanine-resistant gene and mutational analysis of feedback-resistant prephenate dehydratase from Corynebacterium glutamicum[J].Biochem Biophys Res Commun,1996,219(2):537-542.
[40] GU P,YANG F,KANG J,et al.One-step of tryptophan attenuator inactivation and promoter swapping to improve the production of L-tryptophan in Escherichia coli[J].Microb Cell Fact,2012,11(1):30-38.
[41] BáEZVIVEROS J L,OSUNA J,HERNáNDEZCHáVEZ G,et al.Metabolic engineering and protein directed evolution increase the yield of L-phenylalanine synthesized from glucose in Escherichia coli[J].Biotechnol Bioeng,2004,87(4):516-524.
[42] 范代娣,原龙,米钰,等.基因工程菌发酵生产L-苯丙氨酸工艺优化[J].西北大学学报(自然科学版),2002,32(1):33-35.
[43] KHAMDUANG M,PACKDIBAMRUNG K,CHUTMANOP J,et al.Production of l-phenylalanine from glycerol by a recombinant Escherichia coli[J].J Ind Microbiol Biotechn,2009,36(10):1267-1274.
[44] ZHOU H,LIAO X,LIU L,et al.Enhanced L-phenylalanine production by recombinant Escherichia coli BR-42(pAP-B03) resistant to bacteriophage BP-1 via a two-stage feeding approach[J].J Ind Microbiol Biotechn,2011,38(9):1219-1227.
[45] DING D,LIU Y,XU Y,et al.Improving the production of L-phenylalanine by identifying key enzymes through multi-enzyme reaction system in vitro[J].Sci Rep,2016,6:32208.
[46] OH M K,ROHLIN L,KAO K C,et al.Global expression profiling of acetate-grown Escherichia coli[J].J Biol Chem,2002,277(15):13175-13183.
[47] PATNAIK R,LIAO J C.Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield[J].Appl Environ Microbiol,1994,60(11):3903-3908.
[48] CHAO Y P,LAI Z J,CHEN P,et al.Enhanced conversion rate of L-phenylalanine by coupling reactions of aminotransferases and phosphoenolpyruvate carboxykinase in Escherichia coli K-12[J].Biotechnol Prog,1999,15(3):453-458.
[49] LIU Y,ZHUANG Y,DING D,et al.Biosensor-based evolution and elucidation of a biosynthetic pathway in Escherichia coli[J].ACS Synth Biol,2017,6(5):837-848.
[50] BINDER S,SCHENDZIELORZ G,ST?BLER N,et al.A high-throughput approach to identify genomic variants of bacterial metabolite producers at the single-cell level[J].Genome Biol,2012,13(5):R40.
[51] RAMAN S,ROGERS J K,TAYLOR N D,et al.Evolution-guided optimization of biosynthetic pathways[J].Proc Natl Acad Sci USA,2014,111(50):17803-17808.
[52] BECKER J,WITTMANN C.Systems and synthetic metabolic engineering for amino acid production:the heartbeat of industrial strain development[J].Curr Opin Biotechnol,2012,23(5):718-726.
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[54] NOORMAN H.An industrial perspective on bioreactor scale-down:what we can learn from combined large-scale bioprocess and model fluid studies[J].Biotechnol J,2011,6(8):934-943.
[55] THONGCHUANG M,PONGSAWASDI P,CHISTI Y,et al.Design of a recombinant Escherichia coli for producing L-phenylalanine from glycerol[J].World J Microbiol Biotechnol,2012,28(10):2937-2943.
[56] WANG J,HUANG J,SHI J,et al.Fermentation characterization of an L-tryptophan producing Escherichia coli,strain with inactivated phosphotransacetylase[J].Ann Microbiol,2013,63(4):1219-1224.
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[2] RODRIGUEZ A,MARTNEZ J A,FLORES N,et al.Engineering Escherichia coli to overproduce aromatic amino acids and derived compounds[J].Microb Cell Fact,2014,13(1):126.
[3] 汪多仁.L-苯丙氨酸生产与应用[J].发酵科技通讯,2011,40(1):29-36.
[4] BONGAERTS J,KR?MER M,MüLLER U,et al.Metabolic engineering for microbial production of aromatic amino acids and derived compounds[J].Metab Eng,2001,3(4):289-300.
[5] DANIALI G,JINAP S,SANNY M,et al.Effect of amino acids and frequency of reuse frying oils at different temperature on acrylamide formation in palm olein and soy bean oils via modeling system[J].Food Chem,2018,245:1-6.
[6] 何若平,周华,韦萍.L-苯丙氨酸的生产及市场分析[J].精细石油化工进展,2000,12(1):47-49.
[7] 冷崇姣.L-苯丙氨酸的制备与应用前景[J].重庆科技学院学报(社会科学版),2004,19(4):9-11.
[8] TACHIBANA Y,ANDO M,KUZUHARA H.Asymmetric synthesis of α-amino acids by nonenzymatic transamination[J].J Syn Org,1983,42(2):134-142.
[9] 洪泽湖.苯丙氨酸制备技术的进展[J].湖南化工,1997,27(4):11-14.
[10] 齐欣,赵温涛,聂建明,等.DL-苯丙氨酸合成新方法[J].化学工业与工程,2002,19(5):394-397.
[11] OJIMA I,YODA N.N-carbamoyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidines(CAPP):efficient new chiralligands for asymmetric hydrogenation[J].Tetrahedron Lett,1980,21(11):1051-1054.
[12] LIN S H,CHEN C N,JUANG R S.Extraction equilibria and separation of phenylalanine and aspartic acid from water with di(2-ethylhexyl)phosphoric acid[J].J Chem Technol Biotechnol,2006,81(3):406-412.
[13] MENG C C,SHENG Y J,CHEN Q B,et al.Exceptional chiral separation of amino acid modified graphene oxide membranes with high-flux[J].J Membr Sci,2017,526:25-31.
[14] WU H,ZHAO Y Y,N M C,et al.Molecularly imprinted organic-inorganic hybrid membranes for selective separation of phenylalanine isomers and its analogue[J].Sep Purif Technol,2009,68(1):97-104.
[15] ZHANG Z,ZHANG M,LIU Y,et al.Preparation of L-phenylalanine imprinted polymer based on monodisperse hybrid silica microsphere and its application on chiral separation of phenylalanine racemates as HPLC stationary phase[J].Sep Purif Technol,2012,87(10):142-148.
[16] LI D C,CHENG S W,WEI D Z,et al.Production of enantiomerically pure (S)-β-phenylalanine and (R)-β-phenylalanine by penicillin G acylase from Escherichia coli in aqueous medium[J].Biotechnol Lett,2007,29(12):1825-1830.
[17] 甘明哲,何丹,范成英,等.米曲霉氨基酰化酶酶法拆分制备D型芳香族氨基酸[J].应用与环境生物学报,2009,15(5):734-736.
[18] 吴建一,谢亚杰.新型手性相转移催化合成L-苯丙氨酸[J].精细石油化工,2004(1):14-17.
[19] PETERSEN S,MACK C,GRAAF A A D,et al.Metabolic consequences of altered phosphoenolpyruvate carboxykinase activity in Corynebacterium glutamicum reveal anaplerotic regulation mechanisms in vivo[J].Metab Eng 2001,3(4):344-361
[20] YANG Y T,BENNETT G N,SAN K Y.The effects of feed and intracellular pyruvate levels on the redistribution of metabolic fluxes in Escherichia coli[J].Metab Eng,2001,3(2):115-123.
[21] YUAN P,CAO W,WANG Z,et al.Enhancement of L-phenylalanine production by engineered Escherichia coli using phased exponential L-tyrosine feeding combined with nitrogen source optimization[J].J Biosci Bioeng,2015,120(1):36-40.
[22] ANZAWA H,ARAKI K,ITO Y,et al.Enzymatic production of l-phenylalanine through transaminase reaction[J].J Gen Appl Microbiol,1991,7:71-83.
[23] ZHANG C,ZHANG J,KANG Z,et al.Enhanced production of L-phenylalanine in Corynebacterium glutamicum due to the introduction of Escherichia coli wild type gene aroH[J].J Ind Microbiol Biotechnol,2013,40(6):643-651.
[24] YUE H,YUAN Q,WANG W.Enhancement of L-phenylalanine production by β-cyclodextrin[J].J Food Eng,2007,79(3):878-884.
[25] 崔建东,黄皓,乔长晟,等.重组大肠杆菌苯丙氨酸解氨酶稳定性和反式肉桂酸的转化[J].化学反应工程与工艺,2007,23(4):326-330.
[26] GERIGK M,BUJNICKI R,GANPO-NKWENKWA E,et al.Process control for enhanced L-phenylalanine production using different recombinant Escherichia coli strains[J].Biotechnol Bioeng,2002,80(7):746-754.
[27] SHU C H,LIAO C C.Optimization of L-phenylalanine production of Corynebacterium glutamicum under product feedback inhibition by elevated oxygen transfer rate[J].Biotechnol Bioeng,2002,77(2):131-141.
[28] HANG B Z,CUI J D,ZHAO G X,et al.Modeling and optimization of phenylalanine ammonia lyase stabilization in recombinant Escherichia coli for the continuous synthesis of L-phenylalanine on the statistical-based experimental designs[J].J Agric Food Chem,2010,58(5):2795-2800.
[29] RITTMANN D,LINDNER S N,WENDISCH V F.Engineering of a glycerol utilization pathway for amino acid production by Corynebacterium glutamicum[J].Appl Environ Microbiol,2008,74(20):6216-6222.
[30] ZHANG C Z,KANG Z,ZHANG J L,et al.Construction and application of novel feedback-resistant 3-deoxy-D-arabino-heptulosonate-7-phosphate synthases by engineering the N-terminal domain for l-phenylalanine synthesis[J].FEMS Microbiol Lett,2014,353(1):11-18.
[31] 张传志,康振,堵国成,等.重组谷氨酸棒杆菌发酵L-苯丙氨酸培养基的优化[J].微生物学通报,2015,42(1):74-84.
[32] SPRENGER G A.From scratch to value:engineering Escherichia coli, wild type cells to the production of L-phenylalanine and other fine chemicals derived from chorismate[J].Appl Environ Microbiol,2007,75(4):739-749.
[33] LIU Y,LI P,ZHAO K B,et al.Corynebacterium glutamicum contains 3-deoxy-D-arabino-heptulosonate 7-phosphate synthases that display novel biochemical features[J].Appl Environ Microbiol,2008,74(17):5497-5503.
[34] LI P P,LI D F,LIU D,et al.Interaction between DAHP synthase and chorismate mutase endows new regulation on DAHP synthase activity in Corynebacterium glutamicum[J].Appl Environ Microbiol,2013,97(24):10373-10380.
[35] LI P P,LIU Y J,LIU S J.Genetic and biochemical identification of the chorismate mutase from Corynebacterium glutamicum[J].Microbiology,2009,155(10):3382-3391.
[36] EGGELING L,BOTT M.Handbook of Corynebacterium glutamicum[M].Boca Raton:CRC Press,2005.
[37] HATAI S.Mutational analysis of feedback inhibition and catalytic sites of prephenate dehydratase from Corynebacterium glutamicum[J].Arch Microbiol,2004,181(3):237-244.
[38] ZHANG S,WILSON D B,GANEM B.Probing the catalytic mechanism of prephenate dehydratase by site-directed mutagenesis of the Escherichia coli P-protein dehydratase domain[J].Biochemistry,2000,39(16):4722-4728.
[39] CHAN M S,HSU W H.Cloning of m-fluorophenylalanine-resistant gene and mutational analysis of feedback-resistant prephenate dehydratase from Corynebacterium glutamicum[J].Biochem Biophys Res Commun,1996,219(2):537-542.
[40] GU P,YANG F,KANG J,et al.One-step of tryptophan attenuator inactivation and promoter swapping to improve the production of L-tryptophan in Escherichia coli[J].Microb Cell Fact,2012,11(1):30-38.
[41] BáEZVIVEROS J L,OSUNA J,HERNáNDEZCHáVEZ G,et al.Metabolic engineering and protein directed evolution increase the yield of L-phenylalanine synthesized from glucose in Escherichia coli[J].Biotechnol Bioeng,2004,87(4):516-524.
[42] 范代娣,原龙,米钰,等.基因工程菌发酵生产L-苯丙氨酸工艺优化[J].西北大学学报(自然科学版),2002,32(1):33-35.
[43] KHAMDUANG M,PACKDIBAMRUNG K,CHUTMANOP J,et al.Production of l-phenylalanine from glycerol by a recombinant Escherichia coli[J].J Ind Microbiol Biotechn,2009,36(10):1267-1274.
[44] ZHOU H,LIAO X,LIU L,et al.Enhanced L-phenylalanine production by recombinant Escherichia coli BR-42(pAP-B03) resistant to bacteriophage BP-1 via a two-stage feeding approach[J].J Ind Microbiol Biotechn,2011,38(9):1219-1227.
[45] DING D,LIU Y,XU Y,et al.Improving the production of L-phenylalanine by identifying key enzymes through multi-enzyme reaction system in vitro[J].Sci Rep,2016,6:32208.
[46] OH M K,ROHLIN L,KAO K C,et al.Global expression profiling of acetate-grown Escherichia coli[J].J Biol Chem,2002,277(15):13175-13183.
[47] PATNAIK R,LIAO J C.Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield[J].Appl Environ Microbiol,1994,60(11):3903-3908.
[48] CHAO Y P,LAI Z J,CHEN P,et al.Enhanced conversion rate of L-phenylalanine by coupling reactions of aminotransferases and phosphoenolpyruvate carboxykinase in Escherichia coli K-12[J].Biotechnol Prog,1999,15(3):453-458.
[49] LIU Y,ZHUANG Y,DING D,et al.Biosensor-based evolution and elucidation of a biosynthetic pathway in Escherichia coli[J].ACS Synth Biol,2017,6(5):837-848.
[50] BINDER S,SCHENDZIELORZ G,ST?BLER N,et al.A high-throughput approach to identify genomic variants of bacterial metabolite producers at the single-cell level[J].Genome Biol,2012,13(5):R40.
[51] RAMAN S,ROGERS J K,TAYLOR N D,et al.Evolution-guided optimization of biosynthetic pathways[J].Proc Natl Acad Sci USA,2014,111(50):17803-17808.
[52] BECKER J,WITTMANN C.Systems and synthetic metabolic engineering for amino acid production:the heartbeat of industrial strain development[J].Curr Opin Biotechnol,2012,23(5):718-726.
[53] TAKORS R.Scale-up of microbial processes:impacts,tools and open questions[J].J Biotechnol,2012,160(1/2):3-9.
[54] NOORMAN H.An industrial perspective on bioreactor scale-down:what we can learn from combined large-scale bioprocess and model fluid studies[J].Biotechnol J,2011,6(8):934-943.
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