Development of a novel method for analyzing collagen O-glycosylations by hydrazide chemistry

Molecular and Cellular Proteomics

Volumn 11, Issue 6, 2012, Pages

  Taga, Yuki ^a   Kusubata, Masashi ^a   Ogawa Goto, Kiyoko ^a   Hattori, Shunji ^a  

^a NIPPI RESEARCH INSTITUTE OF BIOMATRIX   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGEN TYPE 1; COLLAGEN TYPE 2; FORMIC ACID; HYDRAZIDE; COLLAGEN; DRUG DERIVATIVE; GALACTOSYLHYDROXYLYSINE; GLUCOSYLGALACTOSYLHYDROXYLYSINE; GLYCOPROTEIN; HYDRAZINE DERIVATIVE; HYDROXYLYSINE; PEPTIDE FRAGMENT;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL BOND; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN GLYCOSYLATION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; AFFINITY CHROMATOGRAPHY; AMINO ACID SEQUENCE; ANIMAL; CATTLE; CHEMISTRY; GLYCOSYLATION; ISOLATION AND PURIFICATION; MOLECULAR GENETICS; OXIDATION REDUCTION REACTION; PEPTIDE MAPPING; PROTEIN MOTIF; PROTEIN PROCESSING; STANDARD; TANDEM MASS SPECTROMETRY;

AMINO ACID MOTIFS; AMINO ACID SEQUENCE; ANIMALS; CATTLE; CHROMATOGRAPHY, AFFINITY; COLLAGEN; COLLAGEN TYPE I; COLLAGEN TYPE II; GLYCOPROTEINS; GLYCOSYLATION; HYDRAZINES; HYDROXYLYSINE; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PEPTIDE FRAGMENTS; PEPTIDE MAPPING; PROTEIN PROCESSING, POST-TRANSLATIONAL; TANDEM MASS SPECTROMETRY;

EID: 84862306094     PISSN: 15359476     EISSN: 15359484     Source Type: Journal    
DOI: 10.1074/mcp.M111.010397     Document Type: Article

References (37)

1. Spiro, R. G. (1967) The structure of the disaccharide unit of the renal glomerular basement membrane. J. Biol. Chem. 242, 4813-4823
2. Shinkai, H., and Yonemasu, K. (1979) Hydroxylysine-linked glycosides of human complement subcomponent C1q and various collagens. Biochem. J. 177, 847-852
3. Wang, C., Luosujärvi, H., Heikkinen, J., Risteli, M., Uitto, L., and Myllylä, R. (2002) The third activity for lysyl hydroxylase 3: galactosylation of hydroxylysyl residues in collagens in vitro. Matrix Biol 21, 559-566
4. Schegg, B., Hülsmeier, A. J., Rutschmann, C., Maag, C., and Hennet, T. (2009) Core glycosylation of collagen is initiated by two beta(1-O)galactosyltransferases. Mol. Cell Biol. 29, 943-952
5. Kivirikko, K. I., and Myllylä, R. (1979) Collagen glycosyltransferases. Int Rev Connect Tissue Res 8, 23-72
6. Tenni, R., Valli, M., Rossi, A., and Cetta, G. (1993) Possible role of overglycosylation in the type I collagen triple helical domain in the molecular pathogenesis of osteogenesis imperfecta. Am. J. Med. Genet. 45, 252-256
7. Murray, L. W., Bautista, J., James, P. L., and Rimoin, D. L. (1989) Type II collagen defects in the chondrodysplasias. I. Spondyloepiphyseal dysplasias. Am. J. Hum. Genet. 45, 5-15
8. Butler, W. T. (1982) Methods in Enzymology, vol. 82, 339-346, Academic Press, New York
9. Gooley, A. A., Classon, B. J., Marschalek, R., and Williams, K. L. (1991) Glycosylation sites identified by detection of glycosylated amino acids released from Edman degradation: the identification of Xaa-Pro-Xaa-Xaa as a motif for Thr-O-glycosylation. Biochem. Biophys. Res. Commun. 178, 1194-1201
10. Zachara, N. E., and Gooley, A. A. (2000) Identification of glycosylation sites in mucin peptides by edman degradation. Methods Mol. Biol. 125, 121-128
11. Zhang, H., Li, X. J., Martin, D. B., and Aebersold, R. (2003) Identification and quantification of N-linked glycoproteins using hydrazide chemistry, stable isotope labeling and mass spectrometry. Nat. Biotechnol 21, 660-666
12. Tian, Y., Zhou, Y., Elliott, S., Aebersold, R., and Zhang, H. (2007) Solid-phase extraction of N-linked glycopeptides. Nat. Protoc. 2, 334-339
13. Ramachandran, P., Boontheung, P., Xie, Y., Sondej, M., Wong, D. T., and Loo, J. A. (2006) Identification of N-linked glycoproteins in human saliva by glycoprotein capture and mass spectrometry. J. Proteome. Res. 5, 1493-1503
14. Pan, S., Wang, Y., Quinn, J. F., Peskind, E. R., Waichunas, D., Wimberger, J. T., Jin, J., Li, J. G., Zhu, D., Pan, C., and Zhang, J. (2006) Identification of glycoproteins in human cerebrospinal fluid with a complementary proteomic approach. J. Proteome. Res. 5, 2769-2779
15. Cao, J., Shen, C., Wang, H., Shen, H., Chen, Y., Nie, A., Yan, G., Lu, H., Liu, Y., and Yang, P. (2009) Identification of N-glycosylation sites on secreted proteins of human hepatocellular carcinoma cells with a complementary proteomics approach. J. Proteome. Res. 8, 662-672
16. Zeng, X., Hood, B. L., Sun, M., Conrads, T. P., Day, R. S., Weissfeld, J. L., Siegfried, J. M., and Bigbee, W. L. (2010) Lung cancer serum biomarker discovery using glycoprotein capture and liquid chromatography mass spectrometry. J. Proteome. Res. 9, 6440-6449
17. Nilsson, J., Rüetschi, U., Halim, A., Hesse, C., Carlsohn, E., Brinkmalm, G., and Larson, G. (2009) Enrichment of glycopeptides for glycan structure and attachment site identification. Nat. Methods 6, 809-811
18. Kurogochi, M., Matsushista, T., Amano, M., Furukawa, J., Shinohara, Y., Aoshima, M., and Nishimura, S. (2010) Sialic acid-focused quantitative mouse serum glycoproteomics by multiple reaction monitoring assay. Mol. Cell Proteomics 9, 2354-2368
19. Klement, E., Lipinszki, Z., Kupihár, Z., Udvardy, A., and Medzihradszky, K. F. (2010) Enrichment of O-GlcNAc modified proteins by the periodate oxidation-hydrazide resin capture approach. J. Proteome. Res. 9, 2200-2206
20. Spiro, R. G. (1967) Studies on the renal glomerular basement membrane. Nature of the carbohydrate units and their attachment to the peptide portion. J. Biol. Chem. 242, 1923-1932
21. Michaelsson, E., Malmström, V., Reis, S., Engström, A., Burkhardt, H., and Holmdahl, R. (1994) T cell recognition of carbohydrates on type II collagen. J. Exp. Med. 180, 745-749
22. Light, N. D. (1986) Use of galactose oxidase in labelling hydroxylysine glycosides of collagen. Connect Tissue Res. 15, 221-233
23. Parikka, K., and Tenkanen, M. (2009) Oxidation of methyl alpha-D-galactopyranoside by galactose oxidase: products formed and optimization of reaction conditions for production of aldehyde. Carbohydr Res. 344, 14-20
24. Parikka, K., Leppanen, A. S., Pitkänen, L., Reunanen, M., Willför, S., and Tenkanen, M. (2010) Oxidation of polysaccharides by galactose oxidase. J. Agric Food Chem. 58, 262-271
25. Miller, E. J. (1972) Structural studies on cartilage collagen employing limited cleavage and solubilization with pepsin. Biochemistry 11, 4903-4909
26. Ueno, T., Tanaka, K., Kaneko, K., Taga, Y., Sata, T., Irie, S., Hattori, S., and Ogawa-Goto, K. (2010) Enhancement of procollagen biosynthesis by p180 through augmented ribosome association on the endoplasmic reticulum in response to stimulated secretion. J. Biol. Chem. 285, 29941-29950
27. Shilov, I. V., Seymour, S. L., Patel, A. A., Loboda, A., Tang, W. H., Keating, S. P., Hunter, C. L., Nuwaysir, L. M., and Schaeffer, D. A. (2007) The Paragon Algorithm, a next generation search engine that uses sequence temperature values and feature probabilities to identify peptides from tandem mass spectra. Mol. Cell Proteomics 6, 1638-1655
28. Morgan, P. H., Jacobs, H. G., Segrest, J. P., and Cunningham, L. W. (1970) A comparative study of glycopeptides derived from selected vertebrate collagens. A possible role of the carbohydrate in fibril formation. J. Biol. Chem. 245, 5042-5048
29. Wu, G. Y., Pereyra, B., and Seifter, S. (1981) Specificity of trypsin and carboxypeptidase B for hydroxylysine residues in denatured collagens. Biochemistry 20, 4321-4324
30. Fietzek, P. P., and Kühn, K. (1976) The primary structure of collagen. Int. Rev. Connect Tissue Res. 7, 1-60
31. Butler, W. T., Miller, E. J., and Finch, J. E., Jr. (1976) The covalent structure of cartilage collagen. Amino acid sequence of the NH2-terminal helical portion of the alpha 1 (II) chain. Biochemistry 15, 3000-3006
32. Butler, W. T., Finch, J. E., Jr., and Miller, E. J. (1977) Covalent structure of cartilage collagen. Amino acid sequence of residues 363-551 of bovine alpha1(II) chains. Biochemistry 16, 4981-4990
33. Francis, G., Butler, W. T., and Finch, J. E., Jr. (1978) The covalent structure of cartilage collagen. Amino acid sequence of residues 552-661 of bovine alpha1(II) chains. Biochem. J. 175, 921-930
34. Seyer, J. M., Hasty, K. A., and Kang, A. H. (1989) Covalent structure of collagen. Amino acid sequence of an arthritogenic cyanogen bromide peptide from type II collagen of bovine cartilage. Eur. J. Biochem. 181, 159-173
35. Piszkiewicz, D., Landon, M., and Smith, E. L. (1970) Anomalous cleavage of aspartyl-proline peptide bonds during amino acid sequence determinations. Biochem. Biophys. Res. Commun. 40, 1173-1178
36. Hatton, M. W., and Regoeczi, E. (1976) The proteolytic nature of commercial samples of galactose oxidase. Purification of the enzyme by a simple affinity method. Biochim. Biophys. Acta 438, 339-346
37. Pflieger, D., Przybylski, C., Gonnet, F., Le Caer, J. P., Lunardi, T., Arlaud, G. J., and Daniel, R. (2010) Analysis of human C1q by combined bottom-up and top-down mass spectrometry: detailed mapping of posttranslational modifications and insights into the C1r/C1s binding sites. Mol. Cell Proteomics 9, 593-610