Detection of glycation sites in proteins by high-resolution mass spectrometry combined with isotopic labeling

Analytical Biochemistry

Volumn 400, Issue 2, 2010, Pages 237-243

  Stefanowicz, Piotr ^a   Kijewska, Monika ^a   Kluczyk, Alicja ^a   Szewczuk, Zbigniew ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

Glycation; Isotopic labeling; Mass spectrometry

Indexed keywords

AMINO ACIDS; GLUCOSE; GLYCOSYLATION; ISOTOPES; MASS SPECTROMETRY; MIXTURES; NEURODEGENERATIVE DISEASES; PEPTIDES;

ALZHEIMER'S DISEASE; CLINICAL CHEMISTRY; EQUIMOLAR MIXTURES; GLYCATION; HIGH RESOLUTION MASS SPECTROMETRY; HUMAN SERUM ALBUMINS; ISOTOPIC LABELING; NONENZYMATIC GLYCATION;

ENZYMATIC HYDROLYSIS;

CARBOHYDRATE; CARBON 13; HUMAN SERUM ALBUMIN; LYSINE; POLYPEPTIDE; UBIQUITIN;

AMADORI REARRANGEMENT; AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; ISOTOPE LABELING; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN GLYCOSYLATION; PROTEIN STRUCTURE;

EID: 77950691730     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2010.02.011     Document Type: Article

References (29)

1. Amadori M. Products of condensation between glucose and p-phenetidine I. Atti Accad. Nazl. Lincei 1925, 2:337-345.
2. Thorp S.R., Baynes J.W. Role of the Maillard reaction in diabetes mellitus and diseases of aging. Drugs Aging 1996, 9:69-77.
3. Rohlfing C., Wiedmeyer M.H., Little R. Biological variation of glycohemoglobin. Clin. Chem. 2002, 48:1116-1118.
4. Nathan D.M., Turgeon H., Regan S. Relationship between glycated hemoglobin levels and mean glucose levels over time. Diabetologia 2007, 50:2239-2244.
5. Frolov A., Hoffmann R. Analysis of Amadori peptides enriched by boronic acid affinity chromatography. Ann. NY Acad. Sci. 2008, 1126:253-256.
6. Zhang Q., Tang N., Brock J.W.C., Mottaz H.M., Ames J.M., Baynes J.W., Smith R.D., Metz T.O. Affinity chromatography coupled with electron transfer dissociation mass spectrometry. J. Proteome Res. 2007, 6:2323-2330.
7. Jeric I., Versluis C., Horvat S., Heck A.J.R. Tracing glycoprotein structures: electron ionization tandem mass spectrometric analysis of sugar-peptide adducts. J. Mass Spectrom. 2002, 37:803-811.
8. Stefanowicz P., Boratyński J., Kańska U., Petry I., Szewczuk Z. Evaluation of high temperature glycation of proteins and peptides by electrospray ionization mass spectrometry. Acta Biochim. Pol. 2001, 48:1137-1141.
9. Frolov A., Hoffmann P., Hoffmann R. Fragmentation behavior of glycated peptides derived from d-glucose, d-fructose, and d-ribose in tandem mass spectrometry. J. Mass Spectrom. 2006, 41:1459-1469.
10. Sniatynski M., Rogalski J.C., Hoffman M.D., Kast J. Correlation and convolution analysis of peptide mass spectra. Anal. Chem. 2006, 78:2600-2607.
11. Hoffman M.D., Sniatyński M.J., Rogalski J.C., Le Blanc J.C., Kast J. Multiple neutral loss monitoring (MNM): a multiplexed method for post-translational modification screening. J. Am. Soc. Mass Spectrom. 2006, 17:307-317.
12. Kijewska M., Kluczyk A., Stefanowicz P., Szewczuk Z. Electrospray ionization mass spectrometric analysis of complexes between peptide-derived Amadori products and borate ions. Rapid Commun. Mass Spectrom. 2009, 23:4038-4046.
13. Kelleher N.L., Nicewonger R.B., Begley T.P., McLafferty F.W. Identification of modification sites in large biomolecules by stable isotope labeling and tandem high resolution mass spectrometry: the active site nucleophile of thiaminase I. J. Biol. Chem. 1997, 27:32215-32220.
14. Muller D.R., Schindler P., Towbin H., Wirth U., Voshol H., Hoving S., Steinmetz M.O. Isotope-tagged cross-linking reagents: a new tool in mass spectrometric protein interaction analysis. Anal. Chem. 2001, 73:1927-1934.
15. Ihling C., Schmidt A., Kalkhof S., Schulz D.M., Stingl C., Mechtler K., Haack M., Beck-Sickinger A.G., Cooper D.M., Sinz A. Isotope-labeled cross-linkers and Fourier transform ion cyclotron resonance mass spectrometry for structural analysis of a protein/peptide complex. J. Am. Soc. Mass Spectrom. 2006, 17:1100-1113.
16. Sinz A. Isotope-labeled photoaffinity reagents and mass spectrometry to identify protein-ligand interactions. Angew. Chem. Intl. Ed. 2007, 46:660-662.
17. Boratyński J. Dry reaction of proteins with carbohydrates at 120°C yields neoglycoconjugates. J. Biotechnol. Tech. 1998, 12:707-710.
18. Boratyński J., Roy R. High temperature conjugation of proteins with carbohydrates. Glycoconj. J. 1998, 15:131-138.
19. Stefanowicz P., Kijewska M., Szewczuk Z. Sequencing of peptide-derived Amadori products by the electron capture dissociation method. J. Mass Spectrom. 2009, 44:1047-1052.
20. Lapolla A., Pedele D., Reitano R., Arico N.C. Enzymatic digestion and mass spectrometry in the study of advanced glycation end products/peptides. J. Am. Soc. Mass Spectrom. 2004, 15:496-509.
21. Stefanowicz P., Kapczyńska K., Kluczyk A., Szewczuk Z. A new procedure for the synthesis of peptide-derived Amadori products on a solid support. Tetrahedron Lett. 2007, 48:967-969.
22. P. Stefanowicz, M. Kijewska, K. Kapczyńska, Z. Szewczuk, Methods of the site-selective solid phase synthesis of peptide-derived Amadori products, Amino Acids (in press), doi: 10.1007/s00726-009-0294-z.
23. Johansen M.B., Kiemer L., Brunak S. Analysis and prediction of mammalian protein glycation. Glycobiology 2006, 16:844-853.
24. Zhang Q., Schepmoes A.A., Brock J.W.C., Wu S., Moore R.J., Purvine S.O., Baynes J.W., Smith R.D., Metz T.O. Improved methods for the enrichment and analysis of glycated peptides. Anal. Chem. 2008, 80:9822-9829.
25. Brancia F.L., Bereszczak J.Z., Lapolla A., Fedele D., Baccarin L., Seraglia R., Traldi P. Comprehensive analysis of glycated human serum albumin tryptic peptides by off-line liquid chromatography followed by MALDI analysis on a time-of-flight/curved field reflectron tandem mass spectrometer. J. Mass Spectrom. 2006, 41:1179-1185.
26. Bar-Or D., Bar-Or R., Rael L.T., Gardner D.K., Slone D.S., Craun M.L. Heterogeneity and oxidation status of commercial human albumin preparations in clinical use. Crit. Care Med. 2005, 33:1638-1641.
27. Garlick R.L., Mazer J.S. The principal site of non-enzymatic glycosylation of human serum albumin in vivo. J. Biol. Chem. 1983, 258:6142-6146.
28. Iberg N., Fluckiger R. Nonezymatic glycosylation of albumin in vivo: identification of multiple glycosylated sites. J. Biol. Chem. 1986, 261:13542-13545.
29. Wa C., Cerny R.L., Clarke W.A., Hage D.S. Characterization of glycation adducts on human serum albumin by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clin. Chim. Acta 2007, 385:48-60.