Fructose-induced N-terminal glycation of enkephalins and related peptides

Journal of Peptide Science

Volumn 14, Issue 8, 2008, Pages 936-945

  Jakas, Andreja ^a   Vinković, Marijana ^a   Smrečki, Vilko ^a   Šporec, Maja ^a   Horvat, Štefica ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Enkephalin; Fructose; Glycation; Heyns compound; Imidazolidinone; Maillard reaction; Peptide stability; Reducing sugar

Indexed keywords

ENKEPHALIN; FRUCTOSE; IMIDAZOLINE DERIVATIVE; LEUCINE ENKEPHALIN; METENKEPHALIN; PHOSPHATE BUFFERED SALINE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DIASTEREOISOMER; ENZYME DEGRADATION; ENZYME STABILITY; GLYCATION; MELTING POINT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PH; PRIORITY JOURNAL;

DRUG STABILITY; ENKEPHALINS; FRUCTOSE; GLYCOSYLATION; HUMANS; IMIDAZOLIDINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PEPTIDE FRAGMENTS; REFERENCE STANDARDS; SERUM ALBUMIN; STEREOISOMERISM;

EID: 50449085909     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1029     Document Type: Article

References (26)

1. Gerrard JA. New Aspects of an AGEing chemistry - Recent developments concerning the Maillard reaction. Aust. J. Chem. 2002; 55: 299-310.
2. Ledl F, Schleicher E. New aspects of the Maillard reaction in foods and in the human body. Angew. Chem., Int. Ed. Engl. 1990; 29: 565-594.
3. Horvat Š, Jakas A. Peptide and amino acid glycation: New insights into the Maillard reaction. J. Pept. Sci. 2004; 10: 119-137.
4. Ahmed N. Advanced glycation endproducts - role in pathology of diabetic complications. Diabetes Res. Clin. Pract. 2005; 67: 3-21.
5. Brownlee M. The pathobiology of diabetic complications: a unifying mechanism. Diabetes 2005; 54: 1615-1625.
6. Vlassara H, Palace MR. Diabetes and advanced glycation endproducts. J. Int. Med. 2002; 251: 87-101.
7. Gaby AR. Adverse effects of dietary fructose. Altern. Med. Rev. 2005; 10: 294-306.
8. Schalkwijk CG, Stehouwer CDA, van Hinsbergh VWM. Fructose-mediated non-enzymatic glycation: sweet coupling or bad modification. Diabet. Metab. Res. Rev. 2004; 20: 369-382.
9. Hinton DJS, Ames JM. Site specificity of glycation and carboxymethylation of bovine serum albumin by fructose. Amino Acids 2006; 30: 425-433.
10. Shipar MAH. Formation of the Heyns rearrangement products in dihydroxyacetone and glycine Maillard reaction: a computational study. Food Chem. 2006; 97: 231-243.
11. Suarez G, Rajaram R, Oronsky AL, Gawinowicz MA. Nonenzymatic glycation of bovine serum albumin by fructose (fructation). Comparison with the Maillard reaction initiated by glucose. J. Biol. Chem. 1989; 264: 3674-3679.
12. Heyns K, Paulsen H, Eichstedt R, Rolle M. Uber die Gewinnung von 2-Amino-aldosen durch Umlagerung von Ketosylaminen. Chem. Ber. 1957; 90: 2039-2049.
13. Ahmed N, Furth AJ. Failure of common glycation assays to detect glycation by fructose. Clin. Chem. 1992; 38: 1301-1303.
14. Horvat Š. Opioid peptides and their glycoconjugates: structure-activity relationships. Curr. Med. Chem. CNS Agents 2001; 1: 133-154.
15. Reid RL, Yen SSC. β-Endorphin stimulates the secretion of insulin and glucagon in humans. J. Clin. Endocrinol. Metab. 1981; 52: 592-594.
16. Fallucca F, Tonnarini G, Dibiase N, Dalessandro M, Negri M. Plasma Met-enkephalin levels in diabetic patients - influence of autonomic neuropathy. Metab. Clin. Exp. 1996; 45: 1065-1068.
17. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X. Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision D.02. Gaussian, Inc.: Wallingford, CT, 2004.
18. Mossine V, Barens CL, Glinsky GV, Feather MS. Molecular and crystal structure of N-(2-deoxy-D-aldohexos-2-yl)-glycine (Heyns compounds). Carbohydr. Res. 1996; 284: 11-24.
19. 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.
20. Ardestani A, Yazdanparast R. Cyperus rotundus suppresses AGE formation and protein oxidation in a model of fructose-mediated protein glycoxidation. Int. J. Biol. Macromol. 2007; 41: 572-578.
21. Roščić M, Horvat Š. Transformations of bioactive peptides in the presence of sugars-Characterization and stability studies of the adducts generated via the Maillard reaction. Bioorg. Med. Chem. 2006; 14: 4933-4943.
22. Metz B, Kersten GFA, Baart GJE, de Jong A. Meiring H, ten Hove J, van Steenbergen MJ, Hennink WE, Crommelin DJA, Jiskoot W. Identification of formaldehyde-induced modifications in proteins: reactions with insulin. Bioconjugate Chem. 2006; 17: 815-822.
23. Varga-Defterdarović L, Vikić-Topić D, Horvat Š. Synthesis and characterization of mannose-related imidazolidinone formed by the intramolecular rearrangement of the mannopyranose ester of leucine-enkephalin. J. Chem Soc., Perkin Trans. 1 1999; 2829-2834.
24. Roščić M, Eklund R, Nordmark E-L, Horvat Š, Widmalm G. Stereochemical assignment of diastereomeric imidazolidinone-ring-containing bicyclic sugar-peptide adducts: NMR spectroscopy and molecular calculations. Eur. J. Org. Chem. 2004; 4641-4647.
25. Jakas A, Horvat Š. The effect of glycation on the chemical and enzymatic stabilitiy of the endogenous opioid peptide, leucine-enkephalin, and related fragments. Bioorg. Chem. 2004; 32: 516-526.
26. Jakas A, Horvat Š. Study of degradation pathways of Amadori compounds obtained by glycation of opioid pentapeptide and related smaller fragments: Stability, reactions, and spectroscopic properties. Biopolymers 2003; 69: 421-431.