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Application and microbial preparation of d-valine

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Abstract

d-Valine is an important organic chiral source and has extensive industrial application, which is used as intermediate for the synthesis of agricultural pesticides, semi-synthetic veterinary antibiotics and pharmaceutical drugs. Its derivatives have shown great activity in clinical use, such as penicillamine for the treatment of immune-deficiency diseases, and actinomycin D for antitumor therapy. Fluvalinate, a pyrethroid pesticide made from d-valine, is a broad-spectrum insecticide with low mammalian toxicity. Valnemulin, a semi-synthetic pleuromutilin derivative synthesized from d-valine, is an antibiotic for animals. Moreover, d-valine is also used in cell culture for selectively inhibiting fibroblasts proliferation. Due to its widespread application, d-valine is gaining more and more attention and some approaches for d-valine preparation have been investigated. In comparison with other approaches, microbial preparation of d-valine is more competitive and promising because of its high stereo selectivity, mild reaction conditions and environmental friendly process. So far, microbial preparation of d-valine can be mainly classified into three categories: microbial asymmetric degradation of dl-valine, microbial stereoselective hydrolysis of N-acyl-dl-valine by d-aminoacylase, and microbial specific hydrolysis of dl-5-isopropylhydantoin by d-hydantoinase coupled with d-carbamoylase. In this paper, the industrial application of d-valine and its microbial preparation are reviewed.

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References

  • Anderson RJ, Adams KG, Henrick CA (1985) Synthesis and insecticidal activity of the stereoisomers of α-cyano-3-phenoxybenzyl 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate (Fluvalinate) and related analogues. J Agric Food Chem 33:508–514

    Article  CAS  Google Scholar 

  • Battilotti M, Barberini U (1988) Preparation of d-valine from dl-5-isopropylhydantoin by stereoselective biocatalysis. J Mol Catal 43:343–352

    Article  CAS  Google Scholar 

  • Berner H, Vyplel H (1987) Pleuromutilin derivatives process for their preparation and their use. United States patent, US4675330

  • Cholewinski AJ, Reid JC, McDermott AM, Wilkin GP (1989) Purification of astroglial-cell cultures from rat spinal cord: the use of d-valine to inhibit fibroblast growth. Neurochem Int 15:365–369

    Article  CAS  Google Scholar 

  • Chu W, Shinomiya M, Kamitori KY, Kamitori S, Carlson RG, Weaver RF, Takusagawa F (1994) Role of d-valine residue in the antitumor drug actinomycin D: replacement of d-valines with other d-amino acids changes the DNA binding characteristics and transcription inhibitory activities. J Am Chem Soc 116:7971–7982

    Article  CAS  Google Scholar 

  • Durand F, Bernuau J, Giostra E, Mentha G, Shouval D, Degott C, Benhamou JP, Valla D (2001) Wilson’s disease with severe hepatic insufficiency: beneficial effects of early administration of d-penicillamine. Gut 48:849–852

    Article  CAS  Google Scholar 

  • Elzen PJ, Eischen FA, Baxter JR, Elzen GW, Wilson WT (1999) Detection of resistance in US Varroa jacobsoni Oud. (Mesostigmata: Varroidae) to the acaricide fluvalinate. Apidologie 30:13–17

    Article  CAS  Google Scholar 

  • Feng D, Li X, Pan Q, Wang Z, Chen MH (2010) Synthesis of valnemulin hydrochloride. Chin J Pharm 41:244–246 (in Chinese)

    CAS  Google Scholar 

  • Fuchs SA, Berger R, Klomp LWJ, Koning TJ (2005) d-Amino acids in the central nervous system in health and disease. Mol Genet Metab 85:168–180

    Article  CAS  Google Scholar 

  • Fujii N (2005) d-Amino acid in elderly tissues. Biol Pharm Bull 28:1585–1589

    Article  CAS  Google Scholar 

  • Gao X, Ma Q, Zhu H (2015) Distribution, industrial applications, and enzymatic synthesis of d-amino acids. Appl Microbiol Biotechnol 99:3341–3349

    Article  CAS  Google Scholar 

  • Gilbert SF, Migeon BR (1975) d-Valine as a selective agent for normal human and rodent epithelial cells in culture. Cell 5:11–17

    Article  CAS  Google Scholar 

  • Haarmann T, Spivak M, Weaver D, Weaver B, Glenn T (2002) Effects of fluvalinate and coumaphos on queen honey bees (hymenoptera: apidae) in two commercial queen rearing operations. J Econ Entomol 95:28–35

    Article  CAS  Google Scholar 

  • Hamase K, Morikawa A, Etoh S, Tojo Y, Miyoshi Y, Zaitsu K (2009) Analysis of small amounts of d-amino acids and the study of their physiological functions in mammals. Anal Sci 25:961–968

    Article  CAS  Google Scholar 

  • Henrick CA, Garcia BA, Staal GB, Cerf DC, Anderson RJ, Gill K, Chinn HR, Labovitz JN, Leippe MM, Woo SL, Carney RL, Gordon DC, Kohn GK (1980) 2-Anilino-3-methylbutyrates and 2-(isoindolin-2-yl)-3-methylbutyrates, two novel groups of synthetic pyrethroid esters not containing a cyclopropane ring. Pestic Sci 34:75–80

    Google Scholar 

  • Hongpaisan J (2000) Inhibition of proliferation of contaminating fibroblasts by d-valine in cultures of smooth muscle cells from human myometrium. Cell Biol Int 24:1–7

    Article  CAS  Google Scholar 

  • Huang Q, Li J, Xia L, Xia X, Duan P, Shen J, Ding S (2010) Residue depletion of valnemulin in swine tissues after oral administration. Anal Chim Acta 664:62–67

    Article  CAS  Google Scholar 

  • Kumagai S, Kobayashi M, Yamaguchi S, Kanaya T, Motohashi R, Isobe K (2004) A new d-aminoacylase from Defluvibacter sp. A 131-3. J Mol Catal B-Enzym 30:159–165

    Article  CAS  Google Scholar 

  • Lin P, Su S, Tsai Y, Lee C (2002) Identification and characterization of a new gene from Variovorax paradoxus Iso1encoding N-acyl-d-amino acid amidohydrolase responsible for d-amino acid production. Eur J Biochem 269:4868–4878

    Article  CAS  Google Scholar 

  • Liu Y, Li Q, Hu X, Yang J (2008) Construction and co-expression of polycistronic plasmid enconding d-hydantoinase and d-carbamoylase for the production of d-amino acids. Enzyme Microb Technol 42:589–593

    Article  CAS  Google Scholar 

  • Liu J, Asano Y, Ikoma K, Yamashita S, Hirose Y, Shimoyama T, Takahashi S, Nakayama T, Nishino T (2012) Purification, characterization, and primary structure of a novel N-acyl-d-amino acid amidohydrolase from Microbacterium natoriense TNJL143-2. J Biosci Bioeng 114:391–397

    Article  CAS  Google Scholar 

  • Lucet D, Sabelle S, Kostelitz O, Gall TL, Mioskowski C (1999) Enantioselective synthesis of α-amino acids and monosubstituted 1,2-diamines by conjugate addition of 4-phenyl-2-oxazolidinone to nitroalkenes. Eur J Org Chem 1999:2583–2591

    Article  Google Scholar 

  • Lupoli TJ, Tsukamoto H, Doud EH, Wang TS, Walker S, Kahne D (2011) Transpeptidase-mediated incorporation of d-amino acids into bacterial peptidoglycan. J Am Chem Soc 133:10748–10751

    Article  CAS  Google Scholar 

  • Macher I (1992) Pleuromutilins. United States patent, US5164526

  • Martínez-Gómez AI, Martínez-Rodríguez S, Clemente-Jiménez JM, Pozo-Dengra J, Rodríguez-Vico F, Heras-Vázquez FJL (2007) Recombinant polycistronic structure of hydantoinase process genes in Escherichia coli for the production of optically pure d-amino acids. Appl Environ Microb 73:1525–1531

    Article  Google Scholar 

  • Martinez-Rodriguez S, Heras-Vazquez FJL, Clemente-Jimenez JM, Mingorance-Cazorla L, Rodriguez-Vico F (2002) Complete conversion of d,l-5-monosubstituted hydantoins with a low velocity of chemical racemization into d-amino acids using whole cells of recombinant Escherichia coli. Biotechnol Prog 18:1201–1206

    Article  CAS  Google Scholar 

  • Martínez-Rodríguez S, Martínez-Gómez AI, Rodríguez-Vico F, Clemente-Jiménez JM, Heras-Vázquez FJL (2010) Natural occurrence and industrial application of d-amino acids: an overview. Chem Biodivers 7:1531–1548

    Article  Google Scholar 

  • Mondick JT, Gibiansky L, Gastonguay MR, Skolnik JM, Cole M, Veal GJ, Boddy AV, Adamson PC, Barrett JS (2008) Population pharmacokinetic investigation of actinomycin D in children and young adults. J Clin Pharmacol 48:35–42

    Article  CAS  Google Scholar 

  • Moriguchi M, Sakai K, Miyamoto Y, Wakayama M (1993) Production, purification and characterization of d-aminoacylase from Alcaligenes xylosoxydans subsp. xylosoxydans A-6. Biosci Biotechnol Biochem 57:1149–1152

    Article  CAS  Google Scholar 

  • Nozaki H, Takenaka Y, Kira I, Watanabe K, Yokozeki K (2005) d-Amino acid production by E. coli co-expression three genes encoding hydantoin racemase, d-hydantoinase and N-carbamoyl-d-amino acid amidohydrolase. J Mol Catal B-Enzym 32:213–218

    Article  CAS  Google Scholar 

  • Picciano PT, Johnson B, Walenga RW, Donovan M, Borman BJ, Douglas WHJ, Kreutzer DL (1984) Effects of d-valine on pulmonary artery endothelial cell morphology and function in cell culture. Exp Cell Res 151:134–147

    Article  CAS  Google Scholar 

  • Poulsen SM, Karlsson M, Johansson LB, Vester B (2001) The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome. Mol Microbiol 41:1091–1099

    Article  CAS  Google Scholar 

  • Quistad GB, Staiger LE, Mulholland KM, Schooley DA (1982) Plant metabolism of Fluvalinate [α-cyano-3-phenoxybenzyl 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate]. J Agric Food Chem 30:888–895

    Article  CAS  Google Scholar 

  • Rodríguez-Alonso MJ, Clemente-Jiménez JM, Rodríguez-Vico F, Heras-Vázquez FJL (2015) Rational re-design of the “double-racemase hydantoinase process” for optically pure production of natural and non-natural l-amino acids. Biochem Eng J 101:68–76

    Article  Google Scholar 

  • Sakai K, Obata T, Ideta K, Moriguchi M (1991) Purification and properties of d-aminoacylase from Alcaligenes denitrificans subsp. xylosoxydans MI-4. J Ferment Bioeng 71:79–82

    Article  CAS  Google Scholar 

  • Senuma M, Otsuki O, Sakata N, Furui M, Tosa T (1989) Industrial production of d-aspartic acid and l-alanine from dl-aspartic acid using a pressurized column reactor containing immobilized Pseudomonas dacunhae cells. J Ferment Bioeng 67:233–237

    Article  CAS  Google Scholar 

  • Stindl A, Keller U (1994) Epimerization of the d-valine portion in the biosynthesis of actinomycin D. Biochemistry 33:9358–9364

    Article  CAS  Google Scholar 

  • Susumu T, Ichiro S, Ko O (1965) Optical resolution of dl-valine. United States patent, US3182079

  • Takahashi E, Furui M, Shibatani T (1997) d-Amino acid production from racemic amino acids by a microbial asymmetric degradation. Biotechnol Tech 11:913–916

    Article  CAS  Google Scholar 

  • Umemura I, Yanagiya K, Komatsubara S, Sato T, Tosa T (1992) d-Alanine production from dl-alanine by Candida maltosa with asymmetric degrading activity. Appl Microbiol Biotechnol 36:722–726

    Article  CAS  Google Scholar 

  • Umemura I, Yanagiya K, Komatsubara S, Sato T, Tosa T (1996) A Candida maltosa mutant defective in alanine aminotransferase: isolation and l-alanine assimilation. Appl Microbiol Biotechnol 45:519–524

    CAS  Google Scholar 

  • Van Rijthoven AW, Dijkmans BA, Thè HS, Meijers KA, Montnor-Beckers ZL, Moolenburgh JD, Boers M, Cats A (1991) Comparison of cyclosporine and d-penicillamine for rheumatoid arthritis: a randomized, double blind, multicenter study. J Rheumatol 18:815–820

    Google Scholar 

  • Vranova V, Zahradnickova H, Janous D, Skene KR, Matharu AS, 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 354:21–39

    Article  CAS  Google Scholar 

  • 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 23:71–85

    Article  CAS  Google Scholar 

  • Yagasaki M, Ozaki A (1998) Industrial biotransformations for the production of d-amino acids. J Mol Catal B-Enzym 4:1–11

    Article  CAS  Google Scholar 

  • Yang YB, Lin CS, Tseng CP, Wang YJ, Tsai YC (1991) Purification and characterization of d-aminoacylase from Alcaligenes faecalis DA1. Appl Environ Microb 57:1259–1260

    CAS  Google Scholar 

  • Yang GS, Vázques PP, Frenich AG, Vidal JLM, Aboul-Enein HY (2004) Separation and simultaneous determination of enantiomers of tau-fluvalinate and permethrin in drinking water. Chromatographia 60:523–526

    Article  CAS  Google Scholar 

  • 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 879:3247–3252

    Article  CAS  Google Scholar 

  • Yokozeki K, Kubota K (1987) Mechanism of asymmetric production of d-amino acids from the corresponding hydantoins by Pseudomonas sp. Agric Biol Chem 51:721–728

    CAS  Google Scholar 

  • Yoshioka R, Ohtsuki O, Da-te T, Okamura K, Senuma M (1994) Optical resolution, characterization, and X-ray crystal structures of diastereomeric salts of chiral amino acids with (s)-(-)-1-phenylethanesulfonic acid. Bull Chem Soc Jpn 67:3102–3120

    Article  Google Scholar 

  • Yuan LG, Luo XY, Zhu LX, Wang R, Liu YH (2010) A physiologically based pharmacokinetic model for valnemulin in rats and extrapolation to pigs. J Vet Pharmacol Ther 34:224–231

    Article  Google Scholar 

  • Zhang B, Wang K, Wang Z, Li X, Wang X, Ni J (2010) Design, synthesis and in vitro antitumor activity of novel actinomycin D analogs. Chem J Chin Univ 31:1346–1352

    CAS  Google Scholar 

  • Zhang C, Xin W, Chen M, Bi Y, Gao Z, Zhang J (2015) Isolation and characterization of l-valine-degrading Candida maltosa DLPU-zpb for d-valine preparation from dl-valine. Lett Appl Microbiol 61:453–459

    Article  CAS  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the financial support provided by the Project of Liaoning Provincial Natural Science Foundation (2014026011).

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Authors and Affiliations

  1. School of Biological Engineering, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Ming Chen, Chao Shi, Ziqing Gao & Chunzhi Zhang

  2. College of Life Science, Dalian Nationalities University, Dalian, 116600, People’s Republic of China

    Jing Zhao

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  1. Ming Chen
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Correspondence to Chunzhi Zhang.

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Chen, M., Shi, C., Zhao, J. et al. Application and microbial preparation of d-valine. World J Microbiol Biotechnol 32, 171 (2016). https://doi.org/10.1007/s11274-016-2119-z

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