Distribution, industrial applications, and enzymatic synthesis of d-amino acids
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  • 作者:Xiuzhen Gao (1)
    Qinyuan Ma (2)
    Hailiang Zhu (1)

    1. School of Life Science
    ; Shandong University of Technology ; Zibo ; 255049 ; China
    2. Technology Center
    ; Weifang Ensign Industry Co. ; Ltd ; Changle ; 262499 ; China
  • 关键词:d ; Amino acids ; Enzymatic synthesis ; Asymmetric amination ; d ; Amino acid dehydrogenase
  • 刊名:Applied Microbiology and Biotechnology
  • 出版年:2015
  • 出版时间:April 2015
  • 年:2015
  • 卷:99
  • 期:8
  • 页码:3341-3349
  • 全文大小:695 KB
  • 参考文献:1. Abe, H, Park, J, Fukumoto, Y, Fujita, E, Tanaka, T, Washio, T, Otsuka, S, Shimizu, T, Watanabe, K (1999) Occurrence of d-amino acids in fish sauces and other fermented fish products. Fish Sci 65: pp. 637-641
    2. Akita, H, Suzuki, H, Doi, K, Ohshima, T (2014) Efficient synthesis of d-branched-chain amino acids and their labeled compounds with stable isotopes using d-amino acid dehydrogenase. Appl Microbiol Biotechnol 98: pp. 1135-1143 CrossRef
    3. Asano, Y, Yamaguchi, S (2005) Dynamic kinetic resolution of amino acid amide catalyzed by d-aminopeptidase and 伪-amino-蔚-caprolactam racemase. J Am Chem Soc 127: pp. 7696-7697 CrossRef
    4. Asano, Y, Nakazawa, A, Kato, Y, Kondo, K (1989) Properties of a novel d-stereospecific aminopeptidase from Ochrobactrum anthropi. J Biol Chem 264: pp. 14233-14239
    5. Asano, Y, Ito, H, Dairi, T, Kato, Y (1996) An alkaline d-stereospecific endopeptidase with 尾-lactamase activity from Bacillus cereus. J Biol Chem 271: pp. 30256-30262 CrossRef
    6. Asano Y, Komeda H, Flickinger MC (2009) d -Aminopeptidase and alkaline d -peptidase. In: Encyclopedia of Industrial Biotechnology, 10.1002/9780470054581.eib251 . John Wiley & Sons, Inc. doi:10.1002/9780470054581.eib251
    7. Bae, H-S, Lee, S-G, Hong, S-P, Kwak, M-S, Esaki, N, Soda, K, Sung, M-H (1999) Production of aromatic d-amino acids from 伪-keto acids and ammonia by coupling of four enzyme reactions. J Mol Catal B Enzym 6: pp. 241-247 CrossRef
    8. Bodanszky, M, Perlman, D (1969) Peptide antibiotics. Science 163: pp. 352-358 CrossRef
    9. Bommarius, AS, Schwarm, M, Drauz, K (1998) Biocatalysis to amino acid-based chiral pharmaceuticals-examples and perspectives. J Mol Catal B Enzym 5: pp. 1-11 CrossRef
    10. Brand茫o PFB, Verseck S, Syldatk C (2004) Bioconversion of D,L-tert-leucine nitrile to D-tert-leucine by recombinant cells expressing nitrile hydratase and D-selective amidase. Eng Life Sci 4:547鈥?56
    11. Br眉ckner, H, Hausch, M (1989) Gas chromatographic detection of d-amino acids as common constituents of fermented foods. Chromatographia 28: pp. 487-492 CrossRef
    12. Burkhart, BM, Gassman, RM, Langs, DA, Pangborn, WA, Duax, WL, Pletnev, V (1999) Gramicidin d-conformation, dynamics and membrane ion transport. Pept Sci 51: pp. 129-144 CrossRef
    13. Fotheringham, Taylor PPAH, Ton JLP (1998) Preparation of d -amino acids by direct fermentative means. United States Patent 5728555
    14. Friedman, M (1999) Chemistry, nutrition, and microbiology of d-amino acids. J Agric Food Chem 47: pp. 3457-3479 CrossRef
    15. Fujii, N (2002) d-Amino acids in living higher organisms. Orig Life Evol Biosph 32: pp. 103-127 CrossRef
    16. Gao, X, Chen, X, Liu, W, Feng, J, Wu, Q, Hua, L, Zhu, D (2012) A novel meso-diaminopimelate dehydrogenase from Symbiobacterium thermophilum: overexpression, characterization, and potential for d-amino acid synthesis. Appl Environ Microbiol 78: pp. 8595-8600 CrossRef
    17. Gao, X, Huang, F, Feng, J, Chen, X, Zhang, H, Wang, Z, Wu, Q, Zhu, D (2013) Engineering the meso-diaminopimelate dehydrogenase from Symbiobacterium thermophilum by site saturation mutagenesis for d-phenylalanine synthesis. Appl Environ Microbiol 79: pp. 5078-5081 CrossRef
    18. Gillman, KW, Starrett, JE, Parker, MF, Xie, K, Bronson, JJ, Marcin, LR, McElhone, KE, Bergstrom, CP, Mate, RA, Williams, R, Meredith, JE, Burton, CR, Barten, DM, Toyn, JH, Roberts, SB, Lentz, KA, Houston, JG, Zaczek, R, Albright, CF, Decicco, CP, Macor, JE, Olson, RE (2010) Discovery and evaluation of BMS-708163, a potent, selective and orally bioavailable 纬-secretase inhibitor. Med Chem Lett 1: pp. 120-124 CrossRef
    19. Grenby, TH (1991) Intense sweeteners for the food industry: an overview. Trends Food Sci Technol 2: pp. 2-6 CrossRef
    20. Grifantini, R, Galli, G, Carpani, G, Pratesi, C, Frascotti, G, Grandi, G (1998) Efficient conversion of 5-substituted hydantoins to d-伪-amino acids using recombinant Escherichia coli strains. Microbiology 144: pp. 947-954 CrossRef
    21. Hanson, RL, Johnston, RM, Goldberg, SL, Parker, WL, Goswami, A (2013) Enzymatic preparation of an R-amino acid intermediate for a 纬-secretase inhibitor. Org Process Res Dev 17: pp. 693-700 CrossRef
    22. Heijenoort, JV (2001) Recent advances in the formation of the bacterial peptidoglycan monomer unit. Nat Prod Rep 18: pp. 503-519 CrossRef
    23. Heller B (1982) d -phenylalanine treatment. Unites States Patent 4355044
    24. Hertel C, Hoffmann T, Jakob-Roetne R, Norcross RD (2000) For treatment of diseases associated with amyloidosis, such as alzheimer鈥檚 disease, diabetes mellitus, familial amyloid polyneuropathy, scrapie, and kreuzfeld-jacob disease. United States Patent 6103910
    25. Hils, M, M眉nch, P, Altenbuchner, J, Syldatk, C, Mattes, R (2001) Cloning and characterization of genes from Agrobacterium sp. IP I-671 involved in hydantoin degradation. Appl Microbiol Biotechnol 57: pp. 680-688 CrossRef
    26. Hopkins, DW, Ferguson, KE (1994) Substrate induced respiration in soil amended with different amino acid isomers. Appl Soil Ecol 1: pp. 75-81 CrossRef
    27. Hsu, C-S, Lai, W-L, Chang, W-W, Liaw, S-H, Tsai, Y-C (2002) Structural-based mutational analysis of d-aminoacylase from Alcaligenes faecalis DA1. Protein Sci 11: pp. 2545-2550 CrossRef
    28. Isobe K, Tamauchi H, Fuhshuku K-i, Nagasawa S, Asano Y (2010) A simple enzymatic method for production of a wide variety of d -amino acids using L-amino acid oxidase from / Rhodococcus sp. AIU Z-35-1. Enzyme research 2010
    29. Kato, S, Ishihara, T, Hemmi, H, Kobayashi, H, Yoshimura, T (2011) Alterations in d-amino acid concentrations and microbial community structures during the fermentation of red and white wines. J Biosci Bioeng 111: pp. 104-108 CrossRef
    30. Katz, E, Demain, AL (1977) The peptide antibiotics of Bacillus: chemistry, biogenesis, and possible functions. Bacteriol Rev 41: pp. 449-474
    31. Kim, GJ, Cheon, YH, Kim, H-S (2000) Directed evolution of a novel N-carbamoylase/d-hydantoinase fusion enzyme for functional expression with enhanced stability. Biotechnol Bioeng 68: pp. 211-217 CrossRef
    32. Kobayashi, J, Shimizu, Y, Mutaguchi, Y, Doi, K, Ohshima, T (2013) Characterization of d-amino acid aminotransferase from Lactobacillus salivarius. J Mol Catal B Enzym 94: pp. 15-22 CrossRef
    33. Komeda, H, Asano, Y (2000) Gene cloning, nucleotide sequencing, and purification and characterization of the d-stereospecific amino-acid amidase from Ochrobactrum anthropi SV3. Eur J Biochem 267: pp. 2028-2035 CrossRef
    34. Komeda, H, Asano, Y (2008) A novel d-stereoselective amino acid amidase from Brevibacterium iodinum: gene cloning, expression and characterization. Enzyme Microb Technol 43: pp. 276-283 CrossRef
    35. Komeda, H, Ishikawa, N, Asano, Y (2003) Enhancement of the thermostability and catalytic activity of d-stereospecific amino-acid amidase from Ochrobactrum anthropi SV3 by directed evolution. J Mol Catal B Enzym 21: pp. 283-290 CrossRef
    36. Kumar, J, Sim, V (2014) d-Amino acid-based peptide inhibitors as early or preventative therapy in alzheimer disease. Prion 8: pp. 119-124 CrossRef
    37. Lee, D-C, Kim, H-S (1998) Optimization of a heterogeneous reaction system for the production of optically active d-amino acids using thermostable d-hydantoinase. Biotechnol Bioeng 60: pp. 729-738 CrossRef
    38. Mart铆n, J, Casqueiro, J, Kosalkov谩, K, Marcos, A, Guti茅rrez, AFFS (1999) Penicillin and cephalosporin biosynthesis: mechanism of carbon catabolite regulation of penicillin production. Antonie Leeuwenhoek 75: pp. 21-31 CrossRef
    39. Navab, M, Anantharamaiah, GM, Hama, S, Garber, DW, Chaddha, M, Hough, G, Lallone, R, Fogelman, AM (2002) Oral administration of an Apo A-I mimetic peptide synthesized from d-amino acids dramatically reduces atherosclerosis in mice independent of plasma cholesterol. Circulation 105: pp. 290-292 CrossRef
    40. Okazaki, S, Suzuki, A, Komeda, H, Yamaguchi, S, Asano, Y, Yamane, T (2007) Crystal structure and functional characterization of a d-stereospecific amino acid amidase from Ochrobactrum anthropi SV3, a new member of the penicillin-recognizing proteins. J Mol Biol 368: pp. 79-91 CrossRef
    41. Okazaki, S, Suzuki, A, Mizushima, T, Komeda, H, Asano, Y, Yamane, T (2008) Structures of d-amino acid amidase complexed with l-phenylalanine and with l-phenylalanine amide: insight into the d-stereospecificity of d-amino acid amidase from Ochrobactrum anthropi SV3. Acta Crystallogr D 64: pp. 331-334 CrossRef
    42. Omura T, Furukawara T (2014) Oil-in-water type emulsion skin cosmetic. United States Patent 8607750B2
    43. Pozo, C, Rodelas, B, Escalera, S, Gonz谩lez-L贸pez, J (2002) d, l-Hydantoinase activity of an Ochrobactrum anthropi strain. J Appl Microbiol 92: pp. 1028-1034 CrossRef
    44. Radkov, A, Moe, L (2014) Bacterial synthesis of d-amino acids. Appl Microbiol Biotechnol 98: pp. 1-12 CrossRef
    45. Reich, E (1963) Biochemistry of actinomycins. Cancer Res 23: pp. 1428-1441
    46. Robinson, T (1976) d-Amino acids in higher plants. Life Sci 19: pp. 1097-1102 CrossRef
    47. Sanchez, CJ, Akers, KS, Romano, DR, Woodbury, RL, Hardy, SK, Murray, CK, Wenke, JC (2014) d-Amino acids enhance the activity of antimicrobials against biofilms of clinical wound isolates of Staphylococcus aureus and Pseudomonas aeruginosa. Antimicrob Agents Chemother 58: pp. 4353-4361 CrossRef
    48. Svennerstam, H, Ganeteg, U, Bellini, C, N盲sholm, T (2007) Comprehensive screening of Arabidopsis mutants suggests the lysine histidine transporter 1 to be involved in plant uptake of amino acids. Plant Physiol 143: pp. 1853-1860 CrossRef
    49. Turner, RJ, Aikens, J, Royer, S, DeFilippi, L, Yap, A, Holzle, D, Somers, N, Fotheringham, IG (2004) d-Amino acid tolerant hosts for d-hydantoinase whole cell biocatalysts. Eng Life Sci 4: pp. 517-520 CrossRef
    50. Vedha-Peters, K, Gunawardana, M, Rozzell, JD, Novick, SJ (2006) Creation of a broad-range and highly stereoselective d-amino acid dehydrogenase for the one-step synthesis of d-amino acids. J Am Chem Soc 128: pp. 10923-10929 CrossRef
    51. Veine, D, Yao, H, Stafford, D, Fay, K, Livant, D (2014) A d-amino acid containing peptide as a potent, noncovalent inhibitor of 伪5尾1 integrin in human prostate cancer invasion and lung colonization. Clin Exp Metastasis 31: pp. 379-393 CrossRef
    52. Vranova, V, Zahradnickova, H, Janous, D, Skene, K, Matharu, A, Rejsek, K, Formanek, P (2012) The significance of d-amino acids in soil, fate and utilization by microbes and plants: review and identification of knowledge gaps. Plant Soil 354: pp. 21-39 CrossRef
    53. Wakayama, M, Moriguchi, M (2001) Comparative biochemistry of bacterial N-acyl-d-amino acid amidohydrolase. J Mol Catal B Enzym 12: pp. 15-25 CrossRef
    54. Wakayama, M, Yoshimune, K, Hirose, Y, Moriguchi, M (2003) Production of d-amino acids by N-acyl-d-amino acid amidohydrolase and its structure and function. J Mol Catal B Enzym 23: pp. 71-85 CrossRef
    55. Walters, DE (1995) Using models to understand and design sweeteners. J Chem Educ 72: pp. 680-683 CrossRef
    56. Welch, BD, VanDemark, AP, Heroux, A, Hill, CP, Kay, MS (2007) Potent d-peptide inhibitors of HIV-1 entry. Proc Natl Acad Sci U S A 104: pp. 16828-16833 CrossRef
    57. Yang, H, Zheng, G, Peng, X, Qiang, B, Yuan, J (2003) d-Amino acids and d-Tyr-tRNATyr deacylase: stereospecificity of the translation machine revisited. FEBS Lett 552: pp. 95-98 CrossRef
    58. Yano, S, Haruta, H, Ikeda, T, Kikuchi, T, Murakami, M, Moriguchi, M, Wakayama, M (2011) Engineering the substrate specificity of Alcaligenes d-aminoacylase useful for the production of d-amino acids by optical resolution. J Chromatogr B 879: pp. 3247-3252 CrossRef
    59. Zhang J, Xu Y, Li R (2013) Preparation method of aspoxicillin. China Patent 103333180A
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Biotechnology
    Microbiology
    Microbial Genetics and Genomics
  • 出版者:Springer Berlin / Heidelberg
  • ISSN:1432-0614
文摘
d-Amino acids exist widely in microbes, plants, animals, and food and can be applied in pharmaceutical, food, and cosmetics. Because of their widespread applications in industry, d-amino acids have recently received more and more attention. Enzymes including d-hydantoinase, N-acyl-d-amino acid amidohydrolase, d-amino acid amidase, d-aminopeptidase, d-peptidase, l-amino acid oxidase, d-amino acid aminotransferase, and d-amino acid dehydrogenase can be used for d-amino acids synthesis by kinetic resolution or asymmetric amination. In this review, the distribution, industrial applications, and enzymatic synthesis methods are summarized. And, among all the current enzymatic methods, d-amino acid dehydrogenase method not only produces d-amino acid by a one-step reaction but also takes environment and atom economics into consideration; therefore, it is deserved to be paid more attention.

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