Production of phenylpyruvic acid from l-phenylalanine using an l-amino acid deaminase from Proteus mirabilis: comparison of enzymatic and whole-cell biotransformation approaches

Applied Microbiology and Biotechnology

Volumn 99, Issue 20, 2015, Pages 8391-8402

  Hou, Ying ^a   Hossain, Gazi Sakir ^a   Li, Jianghua ^a   Shin, Hyun dong ^b   Liu, Long ^a   Du, Guocheng ^a  

^a JIANGNAN UNIVERSITY   (China)

^b Georgia Institute of Technology   (United States)

Author keywords

l Amino acid deaminase; Phenylpyruvic acid; Proteus mirabilis; Whole cell biotransformation

Indexed keywords

AMINO ACIDS; BIOCATALYSTS; BIOCONVERSION; CELLS; CYTOLOGY; ESCHERICHIA COLI; PRODUCTIVITY; PROTEINS; PURIFICATION;

COMPARATIVE STUDIES; ESCHERICHIA COLI BL21; L-AMINO ACIDS; PHENYLPYRUVIC ACIDS; PROTEUS MIRABILIS; RECOMBINANT E. COLI; WHOLE CELL BIOCATALYSTS; WHOLE-CELL BIOTRANSFORMATIONS;

ENZYMES;

2 OXOACID; AMINO ACID; DEAMINASE; PHENYLALANINE; PHENYLPYRUVIC ACID; AMMONIA LYASE; RECOMBINANT PROTEIN;

AMINO ACID; BIOTECHNOLOGY; BIOTRANSFORMATION; CATALYST; COLIFORM BACTERIUM; COMPARATIVE STUDY; ENZYME ACTIVITY; MEMBRANE; OPTIMIZATION; ORGANIC ACID;

ARTICLE; BIOCATALYST; BIOTRANSFORMATION; CATALYSIS; COMPARATIVE STUDY; ENZYME ACTIVITY; ENZYME PURIFICATION; ENZYME STABILITY; ESCHERICHIA COLI; NONHUMAN; PH; PROTEIN EXPRESSION; PROTEUS MIRABILIS; SOLUBILIZATION; SYNTHESIS; WHOLE CELL; ENZYMOLOGY; GENE EXPRESSION; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR CLONING;

ESCHERICHIA COLI; PROTEUS MIRABILIS;

AMINO ACIDS; AMMONIA-LYASES; BIOTRANSFORMATION; CLONING, MOLECULAR; ESCHERICHIA COLI; GENE EXPRESSION; PHENYLALANINE; PHENYLPYRUVIC ACIDS; PROTEUS MIRABILIS; RECOMBINANT PROTEINS;

EID: 84941995808     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-015-6757-0     Document Type: Article

References (41)

1. Arachea BT, Sun Z, Potente N, Malik R, Isailovic D, Viola RE (2012) Detergent selection for enhanced extraction of membrane proteins. Protein Expr Purif 86:12–20
2. Bannwarth M, Schulz GE (2003) The expression of outer membrane proteins for crystallization. Biochim Biophys Acta 1610:37–45
3. Bifulco D, Pollegioni L, Tessaro D, Servi S, Molla G (2013) A thermostable L-aspartate oxidase: a new tool for biotechnological applications. Appl Microbiol Biotechnol 97:7285–7295
4. Brodelius P, Nilsson K, Mosbach K (1981) Production of α-keto acids. Part I. Immobilized cells of Trigonopsis variabilis containing D-amino acid oxidase. Appl Biochem Biotechnol 6:293–307
5. Brunhuber NMW, Thoden JB, Blanchard JS, Vanhooke JL (2000) Rhodococcus L-phenylalanine dehydrogenase: kinetics, mechanism, and structural basis for catalytic specifity. Biochemistry 39:9174–9187
6. Butò S, Pollegioni L, D'Angiuro L, Pilone MS (1994) Evaluation of D-amino acid oxidase from Rhodotorula gracilis for the production of α-keto acids: a reactor system. Biotechnol Bioeng 44:1288–1294
7. Carpenter EP, Beis K, Cameron AD, Iwata S (2008) Overcoming the challenges of membrane protein crystallography. Curr Opin Struct Biol 18:581–586
8. Chen H, Gu Z, Zhang H, Wang M, Chen W, Lowther WT, Chen YQ (2013) Expression and purification of integral membrane fatty acid desaturases. PLoS ONE 8:e58139
9. Coban HB, Demirci A, Patterson PH, Elias RJ (2014) Screening of phenylpyruvic acid producers and optimization of culture conditions in bench scale bioreactors. Bioprocess Biosyst Eng 37:2343–2352
10. Das-Bradoo S, Svensson I, Santos J, Plieva F, Mattiasson B, Hatti-Kaul R (2004) Synthesis of alkylgalactosides using whole cells of Bacillus pseudofirmus species as catalysts. J Biotechnol 110:273–285
11. Deng D, Xu C, Sun P, Wu J, Yan C, Hu M, Yan N (2014) Crystal structure of the human glucose transporter GLUT1. Nature 510:121–125
12. des Abbayes H, Salaun JY (2003) Double carbonylation and beyond: systems at work and their organometallic models. Dalton Trans 6:1041–1052
13. Doig SD, Simpson H, Alphand V, Furstoss R, Woodley JM (2003) Characterization of a recombinant Escherichia coli TOP10 pQR239 whole-cell biocatalyst for stereoselective Baeyer-Villiger oxidations. Enzym Microb Technol 32:347–355
14. Drechsel H, Thieken A, Reissbrodt R, Jung G, Winkelmann G (1993) Alpha-keto acids are novel siderophores in the genera Proteus, Providencia, and Morganella and are produced by amino acid deaminases. J Bacteriol 175:2727–2733
15. Du XY, Clemetson KJ (2002) Snake venom L-amino acid oxidases. Toxicon 40:659–665
16. Duerre JA, Chakrabarty S (1975) L-amino acid oxidases of Proteus rettgeri. J Bacteriol 121:656–663
17. Duetz WA, Van Beilen JB, Witholt B (2001) Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis. Curr Opin Biotechnol 12:419–425
18. Fernandez-Lafuente R, Rodriguez V, Guisán JM (1998) The coimmobilization of D-amino acid oxidase and catalase enables the quantitative transformation of D-amino acids (D-phenylalanine) into α-keto acids (phenylpyruvic acid). Enzym Microb Technol 23:28–33
19. Fukuda H, Hama S, Tamalampudi S, Noda H (2008) Whole-cell biocatalysts for biodiesel fuel production. Trends Biotechnol 26:668–673
20. Gao B, Su E, Lin J, Jiang Z, Ma Y, Wei D (2009) Development of recombinant Escherichia coli whole-cell biocatalyst expressing a novel alkaline lipase-coding gene from Proteus sp. for biodiesel production. J Biotechnol 139:169–175
21. Geueke B, Hummel W (2002) A new bacterial L-amino acid oxidase with a broad substrate specificity: purification and characterization. Enzym Microb Technol 31:77–87
22. Hossain GS, Li JH, Shin HD, Chen RR, Du GC, Liu L, Chen J (2013a) Bioconversion of L-glutamic acid to α-ketoglutaric acid by an immobilized whole-cell biocatalyst expressing L-amino acid deaminase from Proteus mirabilis. J Biotechnol 169:112–120
23. Hossain GS, Li JH, Shin HD, Du GC, Liu L, Chen J (2013b) L-Amino acid oxidases from microbial sources: types, properties, functions, and applications. Appl Microbiol Biotechnol 98:1507–1515
24. Koutsopoulos S, Kaiser L, Eriksson HM, Zhang SG (2012) Designer peptide surfactants stabilize diverse functional membrane proteins. Chem Soc Rev 41:1721–1728
25. Leese C, Fotheringham I, Escalettes F, Speight R, Grogan G (2013) Cloning, expression, characterisation and mutational analysis of L-aspartate oxidase from Pseudomonas putida. J Mol Catal B Enzym 85–86:17–22
26. Li XF, Jiang B, Pan BL (2007) Biotransformation of phenylpyruvic acid to phenyllactic acid by growing and resting cells of a Lactobacillus sp. Biotechnol Lett 29:593–597
27. Lin ECC, Pitt B, Civen M, Knox WE (1958) The assay of aromatic amino acid transaminations and keto acid oxidation by the enol borate-tautomerase method. J Biol Chem 233:668–673
28. Marinoni I, Nonnis S, Monteferrante C, Heathcote P, Härtig E, Böttger LH, Trautwein AX, Negri A, Albertini AM, Tedeschi G (2008) Characterization of L-aspartate oxidase and quinolinate synthase from Bacillus subtilis. FEBS J 275:5090–5107
29. Massad G, Zhao H, Mobley HL (1995) Proteus mirabilis amino acid deaminase: cloning, nucleotide sequence, and characterization of aad. J Bacteriol 177:5878–5883
30. Matsumoto T, Takahashi S, Kaieda M, Ueda M, Tanaka A, Fukuda H, Kondo A (2001) Yeast whole-cell biocatalyst constructed by intracellular overproduction of Rhizopus oryzae lipase is applicable to biodiesel fuel production. Appl Microbiol Biotechnol 57:515–520
31. Moustafa IM, Foster S, Lyubimov AY, Vrielink A (2006) Crystal structure of LAAO from Calloselasma rhodostoma with an L-phenylalaniine substrate: insights into structure and mechanism. J Mol Biol 364:991–1002
32. Ninh PH, Honda K, Yokohigashi Y, Okano K, Omasa T, Ohtake H (2013) Development of a continuous bioconversion system using a thermophilic whole-cell biocatalyst. Appl Environ Microbiol 79:1996–2001
33. Okino S, Inui M, Yukawa H (2005) Production of organic acids by Corynebacterium glutamicum under oxygen deprivation. Appl Microbiol Biotechnol 68:475–480
34. Pantaleone DP, Geller AM, Taylor PP (2001) Purification and characterization of an L-amino acid deaminase used to prepare unnatural amino acids. J Mol Catal B Enzym 11:795–803
35. Richter N, Neumann M, Liese A, Wohlgemuth R, Weckbecker A, Eggert T, Hummel W (2010) Characterization of a whole-cell catalyst co-expressing glycerol dehydrogenase and glucose dehydrogenase and its application in the synthesis of L-glyceraldehyde. Biotechnol Bioeng 106:541–552
36. Schuurmann J, Quehl P, Festel G, Jose J (2014) Bacterial whole-cell biocatalysts by surface display of enzymes: toward industrial application. Appl Microbiol Biotechnol 98:8031–8046
37. Szwajcer E, Brodelius P, Mosbach K (1982) Production of α-keto acids: 2. Immobilized whole cells of Providencia sp. PCM 1298 containing L-amino acid oxidase. Enzym Microb Technol 4:409–413
38. Tan Q, Song Q, Zhang Y, Wei D (2007) Characterization and application of D-amino acid oxidase and catalase within permeabilized Pichia pastoris cells in bioconversions. Appl Biochem Biotechnol 136:279–289
39. Toyama MH, Toyama DD, Passero LFD, Laurenti MD, Corbett CE, Tomokane TY, Fonseca FV, Antunes E, Joazeiro PP, Beriam LOS, Martins MAC, Monteiro HSA, Fonteles MC (2006) Isolation of a new L-amino acid oxidase from Crotalus durissus cascavella venom. Toxicon 47:47–57
40. Upadhya R, Bhat S (2000) Stabilization of D-amino acid oxidase and catalase in permeabilized Rhodotorula gracilis cells and its application for the preparation of α-keto acids. Biotechnol Bioeng 68:430–436
41. Villablanca M, Cilento G (1987) Oxidation of phenylpyruvic acid. Biochem Biophys Acta Gen Subj 926:224–230