期刊信息

  • 刊名: 河北师范大学学报(自然科学版)Journal of Hebei Normal University (Natural Science)
  • 主办: 河北师范大学
  • ISSN: 1000-5854
  • CN: 13-1061/N
  • 中国科技核心期刊
  • 中国期刊方阵入选期刊
  • 中国高校优秀科技期刊
  • 华北优秀期刊
  • 河北省优秀科技期刊

生物合成D-丙氨酸研究进展

  • (河北师范大学 生命科学学院,河北 石家庄050024)
  • DOI: 10.13763/j.cnki.jhebnu.nse.202204002

Research Progress in Biosynthesis of D-alanine

摘要/Abstract

摘要:

D-丙氨酸不仅是细菌细胞壁肽聚糖结构中四肽尾的重要成分之一,在药物合成、食品添加剂、化妆品及农业等方面的应用也越来越广泛.由于自然界中并不存在游离形式的D-丙氨酸,因此,D-丙氨酸合成工艺的开发正受到广泛关注.介绍了不同的D-丙氨酸合成技术的优缺点,如化学合成法,微生物发酵法和酶法合成等,并展望了酶法合成D-丙氨酸的发展前景.

Abstract:

D-alanine is one of the key components of the tetrapeptide side chain in the peptidoglycan in bacterial cell wall, and more and more widely used in drug synthesis, food additives, cosmetics and agriculture.Since there is no free form of D-alanine in nature, the development of synthetic process of D-alanine has attracted considerable attention.Here, the advantages and disadvantages of different Dalanine synthesis technologies, such as chemical synthesis, microbial fermentation and enzymatic synthesis, are introduced, and the prospects for the development of enzymatic synthesis of Dalanine are also prospected.

参考文献 53

  • [1] LEE C J, QIU T A, SWEEDLER J V. D-alanine: Distribution, Origin, Physiological Relevance, and Implications in Disease [J]. Biochimica et Biophysica Acta-Proteins and Proteomics, 2020, 1868(11): 140482. doi: 10.1016/j.bbapap.2020.140482
  • [2] GENCHI G. An Overview on D-amino Acids [J]. Amino Acids, 2017, 49(9): 1521-1533. doi: 10.1007/s00726-017-2459-5
  • [3] PAPOUIN T, DUNPHY J M, TOLMAN M, et al. Septal Cholinergic Neuromodulation Tunes the Astrocyte-dependent Gating of Hippocampal NMDA Receptors to Wakefulness [J]. Neuron, 2017, 94(4): 840-854. doi: 10.1016/j.neuron.2017.04.021
  • [4] PLOUX E, FRERET T, BILLARD J M.D-serine in Physiological and Pathological Brain Aging [J]. Biochimica et Biophysica Acta-Proteins and Proteomics, 2021, 1869(1): 140542. doi: 10.1016/j.bbapap.2020.140542
  • [5] SANTILLO A, FALVO S, CHIEFFI P, et al. D-aspartate Induces Proliferative Pathways in Spermatogonial GC-1 Cells [J]. Journal of Cellular Physiology, 2016, 231(2): 490-495. doi: 10.1002/jcp.25095
  • [6] TASSONI R, van der AART L T, UBBINK M, et al.Structural and Functional Characterization of the Alanine Racemase from Streptomyces coelicolor A3(2) [J]. Biochemical and Biophysical Research Communications, 2017, 483(1): 122-128. doi: 10.1016/j.bbrc.2016.12.183
  • [7] MOSCOSO M, GARCA P, CABRAL M P, et al. A D-alanine Auxotrophic Live Vaccine Is Effective Against Lethal Infection Caused by Staphylococcus aureus [J]. Virulence, 2018, 9(1): 604-620. doi: 10.1080/21505594.2017.1417723
  • [8] BODANSZKY M, PERLMAN D. Peptide Antibiotics [J]. Science, 1969, 163(3865): 352-358. doi: 10.1126/science.163.3865.352
  • [9] LIU D, ZHANG L, XUE W, et al. Knockout of the Alanine Racemase Gene in Aeromonas hydrophila HBNUAh01 Results in Cell Wall Damage and Enhanced Membrane Permeability [J]. FEMS Microbiology Letters, 2015, 362(13): fnv089. doi: 10.1093/femsle/fnv089
  • [10] CHESNOKOVA O N, MCPHERSON S A, STEICHEN C T. The Spore-specific Alanine Racemase of Bacillus anthracis and Its Role in Suppressing Germination During Spore Development [J]. Journal of Bacteriology, 2009, 191(4): 1303-1310. doi: 10.1128/jb.01098-08
  • [11] ZHANG Y, LI X, ZHANG C, et al. Production of D-alanine from DL-alanine Using Immobilized Cells of Bacillus subtilis HLZ-68 [J]. World Journal of Microbiology and Biotechnology, 2017, 33: 176. doi: 10.1007/s11274-017-2341-3
  • [12] FRIEDMAN M. Origin, Microbiology, Nutrition, and Pharmacology of D-amino Acids [J]. Chemistry & Biodiversity, 2010, 7(6): 1491-1530. doi: 10.1002/cbdv.200900225
  • [13] SCHIEBER A, BRCKNER H, RUPP-CLASSEN M, et al. Evaluation of D-amino Acid Levels in Rat by Gas Chromatography-selected Ion Monitoring Mass Spectrometry: No Evidence for Subacute Toxicity of Orally Fed D-proline and D-aspartic Acid [J]. Journal of Chromatography B, 1997, 691(1): 1-12. doi: 10.1016/s0378-4347(96)00378-7
  • [14] ZHENG J, LAN X, HUANG L, et al. Kinetic Resolution of N-acetyl-DL-alanine Methyl Ester Using Immobilized Escherichia coli Cells Bearing Recombinant Esterase from Bacillus cereus [J]. Chirality, 2018, 30(7): 907-912. doi: 10.1002/chir.22863
  • [15] DU S, WANG Y, ALATRASH N, et al. Altered Profiles and Metabolism of L- and D-amino Acids in Cultured Human Breast Cancer Cells vs. Non-tumorigenic Human Breast Epithelial Cells [J]. Journal of Pharmaceutical and Biomedical Analysis, 2019, 164: 421-429. doi: 10.1016/j.jpba.2018.10.047
  • [16] FRIEDMAN M, LEVIN C E. Nutritional and Medicinal Aspects of D-amino Acids [J]. Amino Acids, 2012, 42(5): 1553-1582. doi: 10.1007/s00726-011-0915-1
  • [17] 王颖, 李云政.D-丙氨酸的用途及制备方法 [J]. 辽宁化工, 2003, 32(2): 58-60. WANG Ying, LI Yunzheng. Application and Preparation Methods of D-alanine [J]. Liaoning Chemical Industry, 2003, 32(2): 58-60.
  • [18] 王传磊.微生物不对称降解生产D丙氨酸发酵机理及动力学的研究 [D]. 大连:大连工业大学, 2014. WANG Chuanlei. Study on the Fermentation Mechanism and Kinetics of D-alanine Production by Microbial Asymmetric Degradation [D]. Dalian: Dalian Polytechnic University, 2014.
  • [19] 张卫卫, 魏宇, 张宏娟, 等.双酶连续催化生物合成D丙氨酸 [J]. 精细化工, 2017, 34(10): 1132-1138, 1160. doi: 10.13550/j.jxhg.2017.10.009 ZHANG Weiwei, WEI Yu, ZHANG Hongjuan, et al. Double Enzyme Continuous Catalytic Biosynthesis of D-alanine [J]. Fine Chemicals, 2017, 34(10): 1132-1138, 1160.
  • [20] SMITH G M, LEE S A, REILLY K C, et al. Fed-batch Two-phase Production of Alanine by a Metabolically Engineered Escherichia coli [J]. Biotechnology Letters, 2006, 28(20): 1695-1700. doi: 10.1007/s10529-006-9142-3
  • [21] 于瑞莲, 浦军平, 许金国, 等.恒定pH流加发酵法生产高纯度D丙氨酸: 中国, 201310163719.2 [P], 2014-11-12. YU Ruilian, PU Junping, XU Jinguo, et al. A Constant-pH Feeding Fermentation Method for Production of High-Purity D-alanine: China, 201310163719.2 [P], 2014-11-12.
  • [22] LI J, CHEN X, CUI Y, et al. Enzymatic Synthesis of D-alanine from a Renewable Starting Material by Co-immobilized Dehydrogenases [J]. Process Biochemistry, 2018, 66: 126-132. doi: 10.1016/j.procbio.2017.12.008
  • [23] PARK E S, DONG J Y, SHIN J S. Biocatalytic Asymmetric Synthesis of Unnatural Amino Acids Through the Cascade Transfer of Amino Groups from Primary Amines onto Keto Acids [J]. ChemCatChem, 2013, 5(12): 3538-3542. doi: 10.1002/cctc.201300571
  • [24] 张晓斌.生物酶不对称氧化法制备D丙氨酸 [J]. 粮食科技与经济, 2011, 36(4): 37-39. doi: 10.16465/j.gste.2011.04.003 ZHANG Xiaobin. Enzyme Asymmetric Oxidation Reaction Prepare D-alanine [J]. Grain Science and Technology and Economy, 2011, 36(04): 37-39.
  • [25] 黄文忠, 浦家齐, 郑栋.光学活性丙氨酸和叔亮氨酸的不对称合成 [J]. 氨基酸和生物资源, 2005, 27(2): 42-44. doi: 10.3969/j.issn.1006-8376.2005.02.015 HUANG Wenzhong, PU Jiaqi, ZHENG Dong. Asymmetric Synthesis of Optical Active Alanine and Terleucine [J]. Amino Acids & Biotic Resources, 2005, 27(2): 42-44.
  • [26] 谷传洲, 未本美, 郑颖平, 等.不对称转换方法制备D型氨基酸 [J]. 化工时刊, 2002, 12: 21-25. doi: 10.3969/j.issn.1002-154X.2002.12.006 GU Chuanzhou, WEI Benmei, ZHENG Yingping, et al. Preparation of D-amino Acid by Asymmetric Transformation [J]. Chemical Industry Times, 2002, 12: 21-25.
  • [27] 韦萍.D氨基酸的制备研究 [D]. 南京:南京工业大学, 2002. WEI Ping. Study on Preparation of D-amino Acids [D]. Nanjing: Nanjing University of Technology, 2002.
  • [28] 庞秀言, 马勇, 李志远.α-丙氨酸旋光异构体的分离 [J]. 应用化学, 2000, 17(1): 105-106. doi: 10.3969/j.issn.1000-0518.2000.01.031 PANG Xiuyan, MA Yong, LI Zhiyuan. Separation of α-alanine Optical Isomers [J]. Chinese Journal of Applied Chemistry, 2000, 17(1): 105-106.
  • [29] 郑树贵.年产100吨D丙氨酸发酵工厂的设计 [D]. 大连: 大连工业大学, 2014. ZHENG Shugui. Design of D-alanine Fermentation Factory with Annual Production of 100 Tons [D]. Dalian: Dalian Polytechnic University, 2014.
  • [30] 蒋立建, 李建俊.不对称转换法制备D丙氨酸的方法: 中国,200610096375.8 [P]. 2008-01-16. JIANG Lijian, LI Jianjun. Method for Preparation of D-alanine by Asymmetric Transition Method:China, 200610096375.8 [P]. 2008-01-16.
  • [31] 王晓平, 刘一鸣, 王丽娟, 等.米曲氨基酰化酶的纯化及固定化酶法拆分D, L丙氨酸 [J]. 吉林大学自然科学学报, 1998, 10(4): 3-5. WANG Xiaoping, LIU Yiming, WANG Lijuan, et al. Purifies of the Aminoacylase and the Resolution of D, L-alanine by the Method of Immobilized Enzyme [J]. Acta Scientiarum Naturalium Universitatis Jilinensis, 1998, 10(4): 3-5.
  • [32] 刘鹏刚, 张飞, 刘均忠, 等.氨基酰化酶固定化细胞光学拆分DL-丙氨酸 [J]. 精细化工, 2009, 26(4): 345-347, 359. doi: 10.3321/j.issn: 1003-5214.2009.04.008 LIU Penggang, ZHANG Fei, LIU Junzhong, et al. Optical Resolution of DL-alanine by Using Immobilized Aminoacylase Cells [J]. Fine Chemicals, 2009, 26(4): 345-347, 359.
  • [33] 夏仕文, 熊文娟, 韦燕婵, 等. 氨基酸氧化酶催化合成非天然手性氨基酸研究进展 [J]. 分子催化, 2015, 29(3): 288-298. doi: 10.16084/j.cnki.issn1001-3555.2015.03.012 XIA Shiwen, XIONG Wenjuan, WEI Yanchan, et al. Advances in the Amino Acid Oxidase-catalyzed Synthesis of Non-natural Chiral Amino Acids [J]. Journal of Molecular Catalysis, 2015, 29(3): 288-298.
  • [34] SINGH S, GOGOI B K, BEZBARUAH R L. Racemic Resolution of Some DL-amino Acids Using Aspergillus Fumigatus L-amino Acid Oxidase [J]. Current Microbiology, 2011, 63(1): 94-99. doi: 10.1007/s00284-011-9955-8
  • [35] 徐琪寿.氨基酸的化学合成 [J]. 氨基酸杂志, 1983, 4: 17-24. XU Qishou. Chemical Synthesisof Amino Acids [J]. Amino Acids, 1983, 4: 17-24.
  • [36] 方序, 叶俊英.DL丙氨酸发酵研究 [J]. 发酵科技通讯, 1991, 20(4): 30-33. doi: 10.16774/j.cnki.issn.1674-2214.1991.04.006 FANG Xu, YE Junying. Study on the Fermentation Conditions of DL-alanine Producing [J]. Bulletin of Fermentation Science and Technology, 1991, 20(4): 30-33.
  • [37] SMITH G M, LEE S A, REILLY K C, et al. Fed-batch Two-phase Production of Alanine by a Metabolically Engineered Escherichia Coli [J]. Biotechnology Letters, 2006, 28(2): 1695-1700. doi: 10.1007/s10529-006-9142-3
  • [38] 张学礼, 张冬竹.生产DL丙氨酸的工程菌及利用该工程菌生产DL丙氨酸的方法: 中国,201210584472.7 [P]. 2013-04-17. ZHANG Xueli, ZHANG Dongzhu. Engineering Bacteria Producing DL-alanine and Method of Producing DL-alanine by Using Engineering Bacteria: China, 201210584472.7 [P]. 2013-04-17.
  • [39] 于平.海因酶研究新进展 [J]. 生物学杂志, 2005, 22(2): 1-4, 58. doi: 10.3969/j.issn.2095-1736.2005.02.001 YU Ping.New Advances on Hydantoinase [J]. Journal of Biology, 2005, 22(2): 1-4, 58.
  • [40] AGANYANTS H, WEIGEL P, HOVHANNISYAN Y, et al. Rational Engineering of the Substrate Specificity of a Thermostable D-hydantoinase (Dihydropyrimidinase) [J]. High Throughput, 2020, 9(1): 5. doi: 10.3390/ht9010005
  • [41] 董妍玲, 谭新国, 潘学武.海因酶法制备D对羟基苯甘氨酸的研究进展 [J]. 氨基酸和生物资源, 2009, 31(3): 47-52. doi: 10.3969/j.issn.1006-8376.2009.03.014 DONG Yanling, TAN Xinguo, PAN Xuewu. Progress on Production of D-p-hydroxyphenylglycine Using Hydantoinase [J]. Amino Acids & Biotic Resources, 2009, 31(3): 47-52.
  • [42] MORTUZA M, AUNG H L, TAIAROA G, et al. Overexpression of a Newly Identified D-amino Acid Transaminase in Mycobacterium smegmatis Complements Glutamate Racemase Deletion [J]. Molecular Microbiology, 2018, 107(2): 198-213. doi: 10.1111/mmi.13877
  • [43] OPEL-READING H K, MORTUZA M, KRAUSE K L. Detection of D-glutamate Production from the Dual Function Enzyme, 4-amino-4-deoxychorismate Lyase/D-amino Acid Transaminase, in Mycobacterium smegmatis [J]. Bio-Protocol, 2019, 9(1): e3135. doi: 10.21769/BioProtoc.3135
  • [44] GAO X, CHEN X, LIU W, et al. A Novel Meso-diaminopimelate Dehydrogenase from Symbiobacterium thermophilum: Overexpression, Characterization, and Potential for D-amino Acid Synthesis [J]. Applied and Environmental Microbiology, 2012, 78(24): 8595-8600. doi: 10.1128/aem.02234-12
  • [45] CHENG X, CHEN X, FENG J, et al. Structure-guided Engineering of Meso-diaminopimelate Dehydrogenase for Enantioselective Reductive Amination of Sterically Bulky 2-keto Acids [J]. Catalysis Science & Technology, 2018, 8(19): 4994-5002. doi: 10.1039/c8cy01426d
  • [46] LI J, CHEN X, CUI Y, et al. Enzymatic Synthesis of D-alanine from a Renewable Starting Material by Co-immobilized Dehydrogenases [J]. Process Biochemistry, 2018, 66: 126-132. doi: 10.1016/j.procbio.2017.12.008
  • [47] 蒋光玉.DL丙氨酸生产工艺的研究进展 [J]. 精细与专用化学品, 2011, 19(7): 25-28. doi: 10.3969/j.issn.1008-1100.2011.07.007 JIANG Guangyu. Progress in Production Technology of DL-alanine [J]. Fine and Specialty Chemicals, 2011, 19(7): 25-28.
  • [48] GALKIN A, KULAKOYA L, YAMOMOTO H, et al. Conversion of α-keto Acids to D-amino Acids by Coupling of Four Enzyme Reactions [J]. Journal of Fermentation and Bioengineering, 1997, 83(3): 299-300. doi: 10.1016/s0922-338X(97)80997-x
  • [49] GALKIN A, KULAKOYA L, YOSHIMURA T, et al. Synthesis of Optically Active Amino Acids from Alpha-keto Acids with Escherichia coli Cells Expressing Heterologous Genes [J]. Applied Microbiology and Biotechnology, 1997, 63(12): 4651-4656. doi: 10.1128/aem.63.12.4651-4656.1997
  • [50] 鞠建松, 徐书景, 王珊珊, 等. 一种合成DL丙氨酸的三基因共表达载体及应用: 中国, 201711065712.1 [P]. 2021-05-07. JU Jiansong, XU Shujing, WANG Shanshan, et al. Construction and Application of a Triple Genes Co-expression Vector for DL-alanine Synthesis: China, 201711065712.1 [P]. 2021-05-07.
  • [51] XUE Z, HU Y, XU S, et al. Characterization and Preliminary Mutation Analysis of a Thermostable Alanine Racemase from Thermoanaerobacter tengcongensis MB4 [J]. Extremophiles, 2013, 17(4): 611-621. doi: 10.1007/s00792-013-0545-5
  • [52] ISRAR M, LV G, XU S, et al. Biochemical Characterization and Mutational Analysis of Alanine Racemase from Clostridium perfringens [J]. Journal of Bioscience and Bioengineering, 2019, 128(2): 149-155. doi: 10.1016/j.jbiosc.2019.02.003
  • [53] 鞠建松, 韩卿卿, 徐书景, 等. 一种丙氨酸消旋酶的突变体酶蛋白及其制备方法: 中国, 201910691113.3 [P]. 2020-01-10. JU Jiansong, HAN Qingqing, XU Shujing, et al. Mutant Zymoprotein of Alanine Racemase and Preparation Method Thereof: China, 201910691113.3 [P]. 2020-01-10.