Loop engineering of amadoriase II and mutational cooperativity

Applied Microbiology and Biotechnology

Volumn 97, Issue 19, 2013, Pages 8599-8607

  Qian, Yu ^a   Zheng, Jing ^a,b   Lin, Zhanglin ^a  

^a TSINGHUA UNIVERSITY   (China)

^b NANJING INSTITUTE OF ENVIRONMENTAL SCIENCES   (China)

Author keywords

Amadoriase II; Combinatorial active site saturation testing; Focused directed evolution; Fructosyl amine oxidase; High throughput screening; Substrate acceptance

Indexed keywords

ACCEPTANCE TESTS; AMINO ACIDS; ASPERGILLUS; DIAGNOSIS; ENZYMES; MUTAGENESIS;

ACTIVE SITE; AMADORIASE; FOCUSED DIRECTED EVOLUTION; FRUCTOSYL AMINE OXIDASE; HIGH THROUGHPUT SCREENING;

SUBSTRATES;

AMADORIASE II; AMANTADINE; MUTANT PROTEIN; OXIDOREDUCTASE; POLYLYSINE; UNCLASSIFIED DRUG;

DECONVOLUTION; ENZYME; ENZYME ACTIVITY; SATURATION; SUBSTRATE;

ARTICLE; ASPERGILLUS FUMIGATUS; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME ENGINEERING; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; NONHUMAN;

ASPERGILLUS FUMIGATUS;

AMINO ACID OXIDOREDUCTASES; ASPERGILLUS FUMIGATUS; DIRECTED MOLECULAR EVOLUTION; MUTAGENESIS; PROTEIN ENGINEERING; SUBSTRATE SPECIFICITY;

EID: 84885386641     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-4705-4     Document Type: Article

References (29)

1. Baynes JW, Thorpe SR (2000) Glycoxidation and lipoxidation in atherogenesis. Free Radical Biol Med 28:1708-1716. doi: 10.1016/s0891-5849(00) 00228-8
2. Cai Z, Xu W, Xue R, Lin Z (2008) Facile, reagentless and in situ release of Escherichia coli intracellular enzymes by heat-inducible autolytic vector for high-throughput screening. Protein Eng Des Sel 21:681-687. doi: 10.1093/protein/gzn049
3. Collard F, Zhang J, Nemet I, Qanungo KR, Monnier VM, Yee VC (2008) Crystal structure of the deglycating enzyme fructosamine oxidase (amadoriase II). J Biol Chem 283:27007-27016. doi: 10.1074/jbc.M804885200
4. Day JF, Thornburg RW, Thorpe SR, Baynes JW (1979) Non-enzymatic glucosylation of rat albumin - studies in vitro and in vivo. J Biol Chem 254:9394-9400
5. Fujiwara M, J-i S, Koga S, Yoshioka I, Kouzuma T, Imamura S, Kawaguchi T, Arai M (2007) Alteration of substrate specificity of fructosyl-amino acid oxidase from Fusarium oxysporum. Appl Microbiol Biotechnol 74:813-819. doi: 10.1007/s00253-006-0720-z
6. Fujiwara M, Sumitani J, Koga S, Yoshioka I, Kouzuma T, Imamura S, Kawaguchi T, Arai M (2006) Alteration of substrate specificity of fructosyl-amino acid oxidase from Ulocladium sp. JS-103. J Biosci Bioeng 102:241-243. doi: 10.1263/jbb.102.241
7. Garlick RL, Mazer JS (1983) The principal site of non-enzymatic glycosylation of human-serum albumin in vivo. J Biol Chem 258:6142-6146
8. Gerhardinger C, Taneda S, Marion MS, Monnier VM (1994) Isolation, purification, and characterization of an amadori product binding-protein from a Pseudomonas sp. soil strain. J Biol Chem 269:27297-27302
9. Heath MM, Rixon KC, Harding JJ (1996) Glycation-induced inactivation of malate dehydrogenase protection by aspirin and a lens molecular chaperone, alpha-crystallin. Biochim Biophys Acta Mol Basis Dis 1315:176-184. doi: 10.1016/0925-4439(95)00120-4
10. Hirokawa K, Gomi K, Bakke M, Kajiyama N (2003) Distribution and properties of novel deglycating enzymes for fructosyl peptide in fungi. Arch Microbiol 180:227-231. doi: 10.1007/s00203-003-0584-x
11. Hirokawa K, Ichiyanagi A, Kajiyama N (2008) Enhancement of thermostability of fungal deglycating enzymes by directed evolution. Appl Microbiol Biotechnol 78:775-781. doi: 10.1007/s00253-008-1363-z
12. Hirokawa K, Nakamura K, Kajiyama N (2004) Enzymes used for the determination of HbA(1C). FEMS Microbiol Lett 235:157-162. doi: 10.1016/j.femsle.2004.04.027
13. Hodge JE, Rist CE (1953) The amadori rearrangement under new conditions and its significance for non-enzymatic browning reactions. J Am Chem Soc 75:316-322. doi: 10.1021/ja01098a019
14. Kim S, Nibe E, Ferri S, Tsugawa W, Sode K (2010) Engineering of dye-mediated dehydrogenase property of fructosyl amino acid oxidases by site-directed mutagenesis studies of its putative proton relay system. Biotechnol Lett 32:1123-1129. doi: 10.1007/s10529-010-0267-z
15. 1c based on peptide mapping. Clin Chem 43:1944-1951
16. Lin Z, Zheng J (2010) Occurrence, characteristics, and applications of fructosyl amine oxidases (amadoriases). Appl Microbiol Biotechnol 86:1613-1619. doi: 10.1007/s00253-010-2523-5
17. Miura S, Ferri S, Tsugawa W, Kim S, Sode K (2008) Development of fructosyl amine oxidase specific to fructosyl valine by site-directed mutagenesis. Protein Eng Des Sel 21:233-239. doi: 10.1093/protein/gzm047
18. Mossine VV, Glinsky GV, Feather MS (1994) The preparation and characterization of some amadori compounds (1-amino-1-deoxy-d-fructose derivatives) derived from a series of aliphatic omega-amino acids. Carbohydr Res 262:257-270. doi: 10.1016/0008-6215(94)84183-7
19. Reetz MT, Bocola M, Carballeira JD, Zha DX, Vogel A (2005) Expanding the range of substrate acceptance of enzymes: combinatorial active-site saturation test. Angew Chem Int Ed 44:4192-4196. doi: 10.1002/anie.200500767
20. Reetz MT, Sanchis J (2008) Constructing and analyzing the fitness landscape of an experimental evolutionary process. Chembiochem 9:2260-2267. doi: 10.1002/cbic.200800371
21. Sakaue R, Kajiyama N (2003) Thermostabilization of bacterial fructosyl-amino acid oxidase by directed evolution. Appl Environ Microbiol 69:139-145. doi: 10.1128/aem.69.1.139-145.2002
22. Shaklai N, Garlick RL, Bunn HF (1984) Nonenzymatic glycosylation of human-serum albumin alters its conformation and function. J Biol Chem 259:3812-3817
23. Takahashi M, Pischetsrieder M, Monnier VM (1997) Isolation, purification, and characterization of amadoriase isoenzymes (fructosyl amine-oxygen oxidoreductase EC 1.5.3) from Aspergillus sp. J Biol Chem 272:3437-3443
24. Warren MS, Benkovic SJ (1997) Combinatorial manipulation of three key active site residues in glycinamide ribonucleotide transformylase. Protein Eng 10:63-68. doi: 10.1093/protein/10.1.63
25. Wells JA (1990) Additivity of mutational effects in proteins. Biochemistry 29:8509-8517. doi: 10.1021/bi00489a001
26. Wu XL, Chen SG, Petrash JM, Monnier VM (2002) Alteration of substrate selectivity through mutation of two arginine residues in the binding site of amadoriase II from Aspergillus sp. Biochemistry 41:4453-4458. doi: 10.1021/bi025539j
27. Xu L, Li S, Ren C, Cai Z, Lin Z (2006) Heat-inducible autolytic vector for high-throughput screening. BioTechniques 41:319-322. doi: 10.2144/000112219
28. Zheng J, Guan H, Xu L, Yang R, Lin Z (2010) Engineered amadoriase II exhibiting expanded substrate range. Appl Microbiol Biotechnol 86:607-613. doi: 10.1007/s00253-009-2319-7
29. Zheng L, Baumann U, Reymond JL (2004) An efficient one-step site-directed and site-saturation mutagenesis protocol. Nucleic Acids Res 32:e115. doi: 10.1093/nar/gnh110