Enzymatic preparation of d-phenyllactic acid at high space-time yield with a novel phenylpyruvate reductase identified from Lactobacillus sp. CGMCC 9967

Journal of Biotechnology

Volumn 222, Issue , 2016, Pages 29-37

  Xu, Guo Chao ^a   Zhang, Ling Ling ^a   Ni, Ye ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Asymmetric reduction; D phenyllactic acid; Lactobacillus sp. CGMCC 9976; Phenylpyruvate reductase

Indexed keywords

ASYMMETRIC REDUCTION; CO-EXPRESSION SYSTEMS; D-3- PHOSPHOGLYCERATE DEHYDROGENASE; EFFICIENT SYNTHESIS; ENZYMATIC PREPARATION; GLUCOSE DEHYDROGENASE; LACTOBACILLUS SP; PHENYLPYRUVATE REDUCTASE;

BIOTECHNOLOGY;

2 HYDROXYACID DEHYDROGENASE; ALIPHATIC COMPOUND; ATROLACTIC ACID; GLUCOSE DEHYDROGENASE; HYDROXYACID; METAL ION; OXIDOREDUCTASE; OXOACID; PHENYLPYRUVATE REDUCTASE; PHENYLPYRUVIC ACID; PHOSPHOGLYCERATE DEHYDROGENASE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; LACTIC ACID DERIVATIVE; PHENYLPYRUVATE OXIDASE;

ARTICLE; BIOCATALYST; BIOTECHNOLOGICAL PRODUCTION; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME SPECIFICITY; GENE EXPRESSION SYSTEM; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LACTOBACILLUS; MOLECULAR DOCKING; MOLECULAR LIBRARY; NONHUMAN; NUCLEOTIDE SEQUENCE; PH; PHYLOGENY; PRIORITY JOURNAL; PROCESS OPTIMIZATION; REDUCTION; SCREENING; STRUCTURAL HOMOLOGY; SYNTHESIS; TEMPERATURE; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; MOLECULAR MODEL;

BACTERIAL PROTEINS; LACTATES; LACTOBACILLUS; MODELS, MOLECULAR; OXIDOREDUCTASES;

EID: 84958168811     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2015.12.011     Document Type: Article

References (36)

1. Cohen-Arazi N., Katzhendler J., Kolitz M., Domb A.J. Preparation of new α-hydroxy acids derived from amino acids and their corresponding polyesters. Macromolecules 2008, 41:7259-7263.
2. Coppola G.M., Schuster H.F. α-Hydroxy Acids in Enantioselective Synthesis 1997, Wiley-VCH, Weinheim.
3. Dieuleveus V., Lemarinier S., Guéguen M. Antimicrobial spectrum and target site of d-3-phenyllactic acid. Int. J. Food Microbiol. 1998, 40:177-183.
4. Fujii T., Shimizu M., Doi Y., Ito T., Miura D., Wariishi H., Takaya N. Novel fungal phenylpyruvate reductase belongs to d-isomer specific 2-hydroxyacid dehydrogenase family. Biochim. Biophys. Acta 2011, 1814:1669-1676.
5. Gröger H. Enzymatic routes to enantiomerically pure aromatic ö-hydroxy carboxylic acids: a further example for the diversity of biocatalysis. Adv. Synth. Catal. 2001, 343:547-558.
6. Hummel W., Schütte H., Kula M.R. Large-scale production of d-lactate dehydrogenase for the stereospecific reduction of pyruvate and phenylpyruvate. Eur. J. Appl. Microbiol. Biotechnol. 1983, 18:75-85.
7. Hummel W., Schütte H., Kula M.R. d-2-hydroxyisocaproate dehydrogenase from Lactobacillus casei: a new enzyme suitable for stereospecific reduction of 2-ketocarboxylic acids. Appl. Microbiol. Biotechnol. 1985, 21:7-15.
8. Hummel W., Schütte H., Kula M.R. D-(-)-mandelic acid dehydrogenase from Lactobacillus curvatus. Appl. Microbiol. Biotechnol. 1988, 28:433-439.
9. Jiang J.H., Mu W.M., Zhang Tao, Jiang B. Bioconversion of phenylpyruvate to phenyllactate: gene cloning, expression, and enzymatic characterization of d- and l-lactate dehydrogenase from Lactobacillus plantarum SK002. Appl. Biochem. Biotechnol. 2010, 162:242-251.
10. Kawaguchi H., Uematsu K., Ogino C., Teramura H., Niimi-Nakamura S., Tsuge Y., Hasunuma T., Oinuma K.I., Takaya N., Kondo A. Simultaneous saccharification and fermentation of kraft pulp by recombinant E. coli for phenyllactic acid production. Biochem. Eng. J. 2014, 88:188-194.
11. Larissegger-Schnell B., Glueck S.M., Kroutil W., Faber K. Enantiocomplementary deracemization of (±)-2-hydroxy-4-phenylbutanoic acid and (±)-3-phenyllactic acid using lipase-catalyzed kinetic resolution combined with biocatalytic racemization. Tetrahedron 2006, 62:2912-2916.
12. Lavermicocca P., Valerio F., Evidente A., Lazzaroni S., Corsetti A., Gobbetti M. Purification and characterization of novel antifungal compounds from the sourdough Lactobacillus plantarum strain 21B. Appl. Environ. Microbiol. 2000, 66:4084-4090.
13. Mu W.M., Liu F.L., Jia J.H., Chen C., Zhang T., Jiang B. 3-Phenyllactic acid production by substrate feeding and pH-control in fed-batch fermentation of Lactobacillus sp. SK007. Bioresour. Technol. 2009, 100:5226-5229.
14. Mu W.M., Yu S.H., Jiang B., Li X.F. Characterization of d-lactate dehydrogenase from Pediococcus acidilactici that converts phenylpyruvic acid into phenyllactic acid. Biotechnol. Lett. 2012, 34:907-911.
15. Mu W.M., Yu S.H., Zhu L.J., Zhang T., Jiang B. Recent research on 3-phenyllactic acid, a broad-spectrum antimicrobial compound. Appl. Microbiol. Biotechnol. 2012, 95:1155-1163.
16. Razeto A., Kochhar S., Hottinger H., Dauter M., Wilson K.S., Lamzin V.S. Domain closure, substrate specificity and catalysis of d-lactate dehydrogenase from Lactobacillus bulgaricus. J. Mol. Biol. 2002, 318:109-119.
17. Sato, K., Ito, H., Ei, H., Microbial conversion of phenyllactic acid to l-phenylalanine. 1986, Brevet, Ajinomoto Co, Inc. JP 86212293.
18. Schmid A., Hollmann F., Park J.B., Bühler B. The use of enzymes in the chemical industry in Europe. Curr. Opin. Biotechnol. 2002, 13:359-366.
19. Schmidt M., Griengl H. Oxynitrilases from cyanogenesis to asymmetric synthesis. Top. Curr. Chem. 1999, 200:193-226.
20. Singh R.K., Raj I., Pujari R., Gourinath S. Crystal structures and kinetics of Type III 3-phosphoglycerate dehydrogenase reveal catalysis by lysine. FEBS J. 2014, 281:5498-5521.
21. Taguchi H., Ohta T. D-lactate dehydrogenase is a member of the D-iosmer-specific 2-hydroxyacid dehydrogenase family. Cloning, sequencing and expression in E. coli of the D-lactate dehydrogenase gene of Lactobacillus plantarum. J. Biol. Chem. 1991, 266:12588-12594.
22. Tamura Y., Ohkubo A., Iwai S., Wada Y., Shinoda T., Arai K., Mineki S., Iida M., Taguchi H. Two forms of NAD-dependent d-mandelate dehydrogenase in Enterococcus faecalis IAM 10071. Appl. Environ. Microbiol. 2002, 68:947-951.
23. Tokuda C., Ishikura Y., Shigematsu M., Mutoh H., Tsuzuki S., Nakahira Y., Tamura Y., Shinoda T., Arai K., Takahashi O., Taguchi H. Conversion of Lactobacillus pentosus d-lactate dehydrogenase to a d-hydroxyisocaproate dehydrogenase through a single amino acid replacement. J. Bacteriol. 2003, 185:5023-5026.
24. Tuberoso C.I., Bifulco E., Caboni P., Sarais G., Cottiglia F., Floris I. Lumichrome and phenyllactic acid as chemical markers of thistle (Galactites tomentosa Moench) honey. J. Agric. Food Chem. 2011, 59:364-369.
25. Urban F.J., Moore B.S. Synthesis of optically active 2-benzyldihydrobenzopyrans for the hypoglycemic agent englitazone. J. Heterocycl. Chem. 1992, 29:431-438.
26. Wada Y., Iwai S., Tamura Y., Ando T., Shinoda T., Arai K., Taguchi H. A new family of D-2-hydroxyacid dehydrogenases that comprises d-mandelate dehydrogenases and 2-ketopantoate reductases. Biosci. Biotechnol. Biochem. 2008, 72:1087-1094.
27. Wallace A.C., Laskowski R.A., Thornton J.M. LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng. 1995, 8:127-134.
28. Weckwerth W., Miyamoto K., Iinuma K., Krause M., Glinski M., Storm T., Bonse G., Kleinkauf H., Zocher R. Biosynthesis of PF1022A and related cyclooctadepsipeptides. J. Biol. Chem. 2000, 275:17909-17915.
29. Xu G.C., Yu H.L., Zhang X.Y., Xu J.H. Access to optically active aryl halohydrins using a substrate tolerant carbonyl reductase discovered from Kluyveromyces thermotolerans. ACS Catal. 2012, 2:2566-2571.
30. Xu G.C., Yu H.L., Zhang Z.J., Xu J.H. Stereocomplementary bioreduction of β-ketonitrile without ethylated byproduct. Org. Lett. 2013, 15:5408-5411.
31. Xu Y.J., Chen L.G., Duan X.M., Meng Y., Jiang L.Q., Li M.L., Zhao G.L., Li Y. Total synthesis of hirsutellide A. Tetrohedron Lett. 2005, 46:4377-4379.
32. Yun H.D., Choi H.L., Fadnavis N.W., Kim B.G. Stereospecific synthesis of (R)-2-hydroxy carboxylic acids using recombinant E. coli BL21 overexpressing YiaE from E. coli K12 and glucose dehydrogenase from Bacillus subtilis. Biotechnol. Prog. 2005, 21:366-371.
33. Yu S., Jiang H., Jiang B., Mu W.M. Characterization of d-lactate dehydrogenase producing D-3-phenyllactic acid from Pediococcus pentosaceus. Biosci. Biotechnol. Biochem. 2012, 76:853-855.
34. Zheng G.W., Xu J.H. New opportunities for biocatalysis: driving the synthesis of chiral chemicals. Curr. Opin. Biotechnol. 2011, 22:784-792.
35. Zheng Z.J., Ma C.Q., Gao C., Li F.S., Qin J.Y., Zhang H.W., Wang K., Xu P. Efficient conversion of phenylpyruvic acid to phenyllactic acid by using whole cells of Bacillus coagulans SDM. PLoS One 2011, 6:e19030.
36. Zheng Z.J., Sheng B.B., Gao C., Zhang H.W., Qin T., Ma C.Q., Xu P. Highly stereoselective biosynthesis of (R)-α-hydroxy carboxylic acids through rationally re-designed mutation of d-lactate dehydrogenase. Sci. Rep. 2013, 3:e3401.