A mechanistic study on the fragmentation of peptide-derived Amadori products

Journal of Mass Spectrometry

Volumn 44, Issue 10, 2009, Pages 1500-1508

  Stefanowicz, Piotr ^a   Kapczynska, Katarzyna ^a   Jaremko, Mariusz ^b   Jaremko, Łukasz ^b,c   Szewczuk, Zbigniew ^a  

^a UNIVERSITY OF WROC AW   (Poland)

^b INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^c UNIVERSITY OF WARSAW   (Poland)

Author keywords

Amadori rearrangement; Glycation; Mechanism; Microwave synthesis; Neutral losses; Nonenzymatic protein modifications

Indexed keywords

AMADORI REARRANGEMENT; GLYCATION; MICROWAVE SYNTHESIS; NEUTRAL LOSSES; NONENZYMATIC PROTEIN MODIFICATIONS;

AMINES; ATOMS; DEHYDRATION; DEUTERIUM; DEWATERING; HYDROGEN; MICROWAVES; OXYGEN; PEPTIDES;

MOLECULES;

CARBON; FORMALDEHYDE; HYDROGEN;

AMADORI REARRANGEMENT; ARTICLE; DEHYDRATION; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL;

GLYCOPROTEINS; GLYCOSYLATION; GLYCOSYLATION END PRODUCTS, ADVANCED; MODELS, CHEMICAL; PEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 70349849494     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1639     Document Type: Article

References (26)

1. J. W. Baynes, S. R. Thorpe. Role of oxidative stress in diabetic complications: a new perspective on an old paradigm. Diabetes 1999, 48, 1.
2. S. R. Thorpe, J. W. Baynes. Role of the Maillard reaction in diabetes mellitus and diseases of aging. Drugs and Aging 1996, 9, 69.
3. M. Amadori. Products of condensation between glucose and p-phenetidine. I. Atti della Accademia Nazionale dei Lincei 1925, 2, 337.
4. R. Kuhn, F. Weygand. The Amadori rearrangement. Ber. 1937, 70B, 769.
5. A. Cerami. Protein glycation, diabetes, and aging. Recent Progress in Hormone Research 2001, 56, 1.
6. V. M. Monnier. Toward a Maillard reaction theory of aging. Progress in Clinical and Biological Research 1989, 304, 1.
7. A. M. Schmidt, S. D. Yan, S. F. Yan, D. M. Stern. The multiligand receptor RAGE as a progression factor amplifying immune and inflammatory responses. The Journal of Clinical Investigation 2001, 108, 949.
8. Y. Hattori, M. Suzuki, S. Hattori, K. Kasai. Vascular smooth muscle cell activation by glycated albumin (Amadori adducts). Hypertension 2002, 39, 22.
9. A. Frolov, P. Hoffmann, R. Hoffmann. Fragmentation behavior of glycated peptides derived from D-glucose, D-fructose and D-ribose in tandem mass spectrometry. Journal of Mass Spectrometry 2006, 41, 1459.
10. P. Stefanowicz, J. Boratynski, U. Kanska, I. Petry, Z. Szewczuk. Evaluation of high temperature glycation of proteins and peptides by electrospray ionization mass spectrometry. Acta Biochimica Polonica 2001, 48, 1137.
11. I. Jeric, C. Versluis, S. Horvat, A. J. R. Heck. Tracing glycoprotein structures: electron ionization tandem mass spectrometric analysis of sugar-peptide adducts. Journal of Mass Spectrometry 2002, 37, 803.
12. P. Stefanowicz, K. Kapczynska, A. Kluczyk. Z. Szewczuk. A new procedure for the synthesis of peptide-derived Amadori products on a solid support. Tetrahedron Letters 2007, 48, 967.
13. A. Frolov, D. Singer, R. J. Hoffmann. Site-specific synthesis of Amadori-modified peptides on solid phase. Peptide Science 2006, 12, 389.
14. P. Stefanowicz, Z. Szewczuk. Studies on glycation of peptides on solid support. Peptides 2004. Proceedings of the Third International and Twenty-Eighth European Peptide Symposium. Kenes International: Israel, 2005, 605.
15. T. L. Mega, S. Cortez, R. L. Van Etten. The O-18 isotope shift in C-13 nuclear magnetic-resonance spectroscopy.13. oxygen-exchange at the anomeric carbon of deuterium-glucose, deuterium-mannose, and deuterium-fructose. Journal of Organic Chemistry 1990, 55, 522.
16. I. P. Csonka, B. Paizs, G. Lendvay, S. Suhai. Suhai Proton mobility in protonated peptides: a joint molecular orbital and RRKM study. Rapid Communications in Mass Spectrometry 2000, 14, 417.
17. B. Paizs, I. P. Csonka, G. Lendvay, S. Suhai. Proton mobility in protonated glycylglycine and N-formylglycylglycinamide: a combined quantum chemical and RKKM study. Rapid Communications in Mass Spectrometry 2001, 15, 637.
18. D. Molle, F. Morgan, S. Bouhallab, J. Leonil. Selective detection of lactolated peptides in hydrolysates by liquid chromatography/electrospray tandem mass spectrometry. Analytical Biochemistry 1998, 259, 152.
19. M. J. Antal, W. S. Mok, G. N. Richards. Kinetic studies of the reaction of ketoses and aldoses in water at high temperatures. 1.Mechanism of formation of 5-(hydroxymethyl)-2-furylaldehyde from D-fructose and sucrose. Carbohydrate Research 1990, 199, 91.
20. Y. Roman-Leskhov, J. N. Chheda, J. A. Dumesic. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312, 1993.
21. C. Perez Locas, V. Yaylayan. Isotope labelling studies on the formation of 5-hydroxymethyl)-2-furaldehyde (HMF) from sucrose by Py-GC/MS. Journal of Agricultural and Food Chemistry 2008, 56, 6717.
22. A. R. Dongre, J. L. Jones, A. Somogyi, V. H. Wysocki. Fragmentation efficiencies of peptide ions following low energy collisional activation. Journal of the American Chemical Society 1996, 118, 8365.
23. T. J. Jorgensen, H. Gardsvoll, M. Ploug, P. Roepstorff. Intramolecular migration of amide hydrogens in protonated peptides upon collisional activation. Journal of the American Chemical Society 2005, 127, 2785.
24. S. Horvat, A. Jakas. Peptide and amino acid glycation: new insights into the Maillard reaction. Journal of Peptide Science 2004, 10, 119.
25. A. Jakas, S. Horvat. Synthesis and C-13 NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine-enkephalin. Journal of the Chemical Society: Perkin Transactions 2 1994, 5, 789.
26. F. W. McLafferty, F. Turecek. Interpretation of Mass Spectra. University Science Books, Sausalito: California, 1993, 264.