Motif-based search for a novel fructosyl peptide oxidase from genome databases

Biotechnology and Bioengineering

Volumn 106, Issue 3, 2010, Pages 358-366

  Kim, Seungsu ^a   Ferri, Stefano ^a   Tsugawa, Wakako ^a   Mori, Kazushige ^b   Sode, Koji ^a,b  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b Ultizyme International Ltd   (Japan)

Author keywords

Biosensor; Diabetes; Fructosyl amino acid oxidase (FAOD); Fructosyl peptide oxidase (FPOX); Hemoglobin A1c (HbA1c)

Indexed keywords

AMINO ACID SEQUENCE; FLEXIBLE SURFACES; FRUCTOSYL AMINO ACID OXIDASE; FRUCTOSYL AMINO ACID OXIDASE (FAOD); FRUCTOSYL PEPTIDE OXIDASE; FRUCTOSYL PEPTIDE OXIDASE (FPOX); GENOME DATABASE; HIGH SPECIFICITY; MODEL COMPOUND; PHAEOSPHAERIA NODORUM; RECOMBINANT PROTEIN; SITE DIRECTED MUTAGENESIS; SPECIFIC SEQUENCES; STRUCTURAL MODELING;

AMINO ACIDS; BIOSENSORS; ESCHERICHIA COLI; HEMOGLOBIN; ORGANIC ACIDS; PEPTIDES; PHOSPHATASES; SEARCH ENGINES; THREE DIMENSIONAL;

GENE ENCODING;

FRUCTOSYL PEPTIDE OXIDASE; HEMOGLOBIN A1C; OXIDOREDUCTASE; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; ASCOMYCETES; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME STABILITY; ENZYME STRUCTURE; ESCHERICHIA COLI; GENE EXPRESSION; GENETIC CODE; GENETIC DATABASE; NONHUMAN; NUCLEOTIDE SEQUENCE; PHAEOSPHAERIA NODORUM; PROTEIN GLYCOSYLATION; PROTEIN MOTIF; SEQUENCE ALIGNMENT; SITE DIRECTED MUTAGENESIS; THERMOSTABILITY;

AMINO ACID MOTIFS; AMINO ACID OXIDOREDUCTASES; AMINO ACID SEQUENCE; ASCOMYCOTA; BASE SEQUENCE; CLONING, MOLECULAR; COMPUTATIONAL BIOLOGY; DATABASES, NUCLEIC ACID; ESCHERICHIA COLI; FUNGAL PROTEINS; GENOME, FUNGAL; KINETICS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT PROTEINS; SEQUENCE ALIGNMENT; SUBSTRATE SPECIFICITY;

ESCHERICHIA COLI; PHAEOSPHAERIA NODORUM;

EID: 77953569307     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.22710     Document Type: Article

References (45)

1. Aiyar A, Xiang Y, Leis J. 1996. Site-directed mutagenesis using overlap extension PCR. Methods Mol Biol 57:177-191.
2. Akazawa S, Karino T, Yoshida N, Katsuragi T, Tani Y. 2004. Functional analysis of fructosyl-amino acid oxidases of Aspergillus oryzae. Appl Environ Microbiol 70:5882-5890.
3. Bowie JU, Lüthy R, Eisenberg D. 1991. A method to identify protein sequences that fold into a known three-dimensional structure. Science 253:164-170.
4. 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.
5. Deleage G, Blanchet C, Geourjon C. 1997. Protein structure prediction. Implications for the biologist. Biochimie 79:681-686.
6. Ferri S, Miura S, Sakaguchi A, Ishimura F, Tsugawa W, Sode K. 2004. Cloning and expression of fructosyl-amine oxidase from marine yeast Pichia species N1-1. Mar Biotechnol (NY) 6:625-632.
7. Ferri S, Sakaguchi A, Goto H, Tsugawa W, Sode K. 2005. Isolation and characterization of a fructosyl-amine oxidase from an Arthrobacter sp. Biotechnol Lett 27:27-32.
8. Ferri S, Kim S, Tsugawa W, Sode K. 2009. Review of fructosyl amino acid oxidase engineering research: A glimpse into the future of hemoglobin A1c biosensing. J Diabetes Sci Technol 3:585-592.
9. 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.
10. Fujiwara M, Sumitani J, 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.
11. Hirokawa K, Kajiyama N. 2002. Recombinant Agrobacterium AgaE-like protein with fructosyl amino acid oxidase activity. Biosci Biotechnol Biochem 66:2323-2329.
12. Hirokawa K, Gomi K, Bakke M, Kajiyama N. 2003a. Distribution and properties of novel deglycating enzymes for fructosyl peptide in fungi. Arch Microbiol 180:227-231. (Pubitemid 37102721)
13. Hirokawa K, Gomi K, Kajiyama N. 2003b. Molecular cloning and expression of novel fructosyl peptide oxidases and their application for the measurement of glycated protein. Biochem Biophys Res Commun 311:104-111. (Pubitemid 37297895)
14. Hirokawa K, Nakamura K, Kajiyama N. 2004. Enzymes used for the determination of HbA1C. FEMS Microbiol Lett 235:157-162.
15. Hirokawa K, Ichiyanagi A, Kajiyama N. 2008. Enhancement of thermostability of fungal deglycating enzymes by directed evolution. Appl Microbiol Biotechnol 78:775-781.
16. Horiuchi T, Kurokawa T. 1991. Purification and properties of fructosylamine oxidase from Aspergillus sp. 1005. Agric Biol Chem 55:333-338.
17. Horiuchi T, Kurokawa T, Saito N. 1989. Purification and properties of fructosyl-amino acid oxidase from Corynebacterium sp. 2-4-1. Agric Biol Chem 53:103-110.
18. Iberg N, Fluckiger R. 1986. Nonenzymatic glycosylation of albumin in vivo-Identification of multiple glycosylated sites. J Biol Chem 261:3542-3545. (Pubitemid 17196372)
19. Jeppsson JO, Kobold U, Barr J, Finke A, Hoelzel W, Hoshino T, Miedema K, Mosca A, Mauri P, Paroni R, Thienpont L, Umemoto M, Weykamp C. 2002. Approved IFCC reference method for the measurement of HbA1c in human blood. Clin Chem Lab Med 40:78-89.
20. Johnson RN, Metcalf PA, Baker JR. 1983. Fructosamine - A new approach to the estimation of serum glycosylprotein - An index of diabetic control. Clinica Chimica Acta 127:87-95.
21. Keil P, Mortensen HB, Christophersen C. 1985. Fructosylvaline. A simple model of the N-terminal residue of human haemoglobin A1c. Acta Chem Scand B 39:191-193.
22. Kim S, Miura S, Ferri S, Tsugawa W, Sode K. 2009. Cumulative effect of amino acid substitution for the development of fructosyl valine-specific fructosyl amine oxidase. Enzyme Microb Technol 44:52-56.
23. Larkin MA, Blackshields G, Brown NP, Chenna R, McGettigan PA, McWilliam H, Valentin F, Wallace IM, Wilm A, Lopez R, Thompson JD, Gibson TJ, Higgins DG. 2007. Clustal W and Clustal X version 2.0. Bioinformatics 23:2947-2948.
24. Liu LM, Hood S, Wang Y, Bezverkov R, Dou C, Datta A, Yuan C. 2008. Direct enzymatic assay for %HbA1c in human whole blood samples. Clin Biochem 41:576-583.
25. Lu G, Moriyama EN. 2004. Vector NTI, a balanced all-in-one sequence analysis suite. Brief Bioinform 5:378-388.
26. Lüthy R, Bowie JU, Eisenberg D. 1992. Assessment of protein models with three-dimensional profiles. Nature 356:83-85.
27. Martí-Renom MA, Stuart AC, Fiser A, Sánchez R, Melo F, Sali A. 2000. Comparative protein structure modeling of genes and genomes. Annu Rev Biophys Biomol Struct 29:291-325. (Pubitemid 30599596)
28. Miura S, Ferri S, Tsugawa W, Kim S, Sode K. 2006. Active site analysis of fructosyl amine oxidase using homology modeling and site-directed mutagenesis. Biotechnol Lett 28:1895-1900. (Pubitemid 44744797)
29. 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. (Pubitemid 351431051)
30. Molinaro RJ. 2008. Targeting HbA1c: Standardization and clinical laboratory measurement. Med Lab Obs 40:10-14, 16-19.
31. Ogawa K, StollnerD, Scheller F, Warsinke A, Ishimura F, TsugawaW, Ferri S, Sode K. 2002. Development of a flow-injection analysis (FIA) enzyme sensor for fructosyl amine monitoring. Anal Bioanal Chem 373:211-214. (Pubitemid 34756932)
32. Sakaguchi A, Tsugawa W, Ferri S, Sode K. 2003. Development of highlysensitive fructosyl-valine enzyme sensor employing recombinant fructosyl amine oxidase. Electrochemistry 71:442-445.
33. Sakurabayashi I, Watano T, Yonehara S, Ishimaru K, Hirai K, Komori T, Yagi M. 2003. New enzymatic assay for glycohemoglobin. Clin Chem 49:269-274.
34. Schnedl WJ, Krause R, Halwachs-Baumann G, Trinker M, Lipp RW, Krejs GJ. 2000. Evaluation of HbA1c determination methods in patients with hemoglobinopathies. Diabetes Care 23:339-344. (Pubitemid 30131741)
35. Sode K, Ishimura F, Tsugawa W. 2001. Screening and characterization of fructosyl-valine-utilizing marine microorganisms. Mar Biotechnol (NY) 3:126-132. (Pubitemid 32925902)
36. Takahashi M, Pischetsrieder M, Monnier VM. 1997a. Isolation, purification, and characterization of amadoriase isoenzymes (fructosyl amine-oxygen oxidoreductase EC 1.5.3) from Aspergillus sp. J Biol Chem 272:3437-3443.
37. Takahashi M, Pischetsrieder M, Monnier VM. 1997b. Molecular cloning and expression of amadoriase isoenzyme (fructosyl amine:oxygen oxidoreductase, EC 1.5.3) from Aspergillus fumigatus. J Biol Chem 272:12505-12507.
38. Tanaka Y, Atsumi Y, Matsuoka K, Mokubo A, Asahina T, Hosokawa K, Shimada S, Matsunaga H, Takagi M, Ogawa O. 2001. Usefulness of stable HbA1c for supportive marker to diagnose diabetes mellitus in Japanese subjects. Diabetes Res Clin Pr 53:41-45.
39. Thompson JD, Higgins DG, Gibson TJ. 1994. CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680.
40. Tsugawa W, Ishimura F, Ogawa K, Sode K. 2000. Development of an enzyme sensor utilizing a novel fructosyl amine oxidase from a marine yeast. Electrochemistry 68:869-871.
41. Tsugawa W, Ogawa K, Ishimura F, Sode K. 2001. Fructosyl amine sensing based on Prussian blue modified enzyme electrode. Electrochemistry 69:973-975.
42. Yoshida N, Sakai Y, Serata M, Tani Y, Kato N. 1995. Distribution and properties of fructosyl amino acid oxidase in fungi. Appl Environ Microbiol 61:4487-4489.
43. Yoshida N, Sakai Y, Isogai A, Fukuya H, Yagi M, Tani Y, Kato N. 1996. Primary structures of fungal fructosyl amino acid oxidases and their application to the measurement of glycated proteins. Eur J Biochem 242:499-505.
44. Yoshida N, Akazawa S, Katsuragi T, Tani Y. 2004. Characterization of two fructosyl-amino acid oxidase homologs of Schizosaccharomyces pombe. J Biosci Bioeng 97:278-280.
45. Yoshida N, Akazawa S, Karino T, Ishida H, Hata Y, Katsuragi T, Tani Y, Takagi H. 2007. Functional analysis of genes encoding putative oxidoreductases in Aspergillus oryzae, which are similar to fungal fructosyl-amino acid oxidase. J Biosci Bioeng 104:424-427.