Formation of arginine modifications in a model system of N α- Tert -butoxycarbonyl (Boc)-arginine with methylglyoxal

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 1, 2011, Pages 394-401

  Klöpfer, Antje ^a   Spanneberg, Robert ^a   Glomb, Marcus A ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

2 amino 5 (2 amino 4 hydro 4 methyl 5 imidazolinone 1 yl)pentanoic acid; Maillard reaction; Methylglyoxal arginine modifications; N 7 (1 carboxyethyl)arginine

Indexed keywords

ALDOL CONDENSATION; ARGININE MODIFICATION; ARGPYRIMIDINE; CATION EXCHANGE CHROMATOGRAPHY; DICARBONYL COMPOUNDS; HIGH RESOLUTION MASS SPECTROMETRY; IMIDAZOLINONE; ISOLATION AND PURIFICATION; KINETIC STUDY; MAILLARD REACTION; METHYLGLYOXAL; MODEL SYSTEM; N 7-(1-CARBOXYETHYL)ARGININE; PENTANOIC ACID; PHYSIOLOGICAL CONDITION; REACTION PATHWAYS; REACTION SCHEMES;

ARGININE; CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION INTERMEDIATES; REACTION KINETICS; RESONANCE; SATURATED FATTY ACIDS;

AMINO ACIDS;

ARGININE; DRUG DERIVATIVE; FOOD ADDITIVE; METHYLGLYOXAL; TERT BUTYLOXYCARBONYL ARGININE; TERT-BUTYLOXYCARBONYL-ARGININE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; KINETICS;

ARGININE; FOOD ADDITIVES; KINETICS; MODELS, CHEMICAL; PYRUVALDEHYDE;

EID: 78651113258     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf103116c     Document Type: Article

References (23)

1. Hayashi, T.; Shibamoto, T. Analysis of methylglyoxal in foods and beverages J. Agric. Food Chem. 1985, 33, 1090-1093
2. Mavric, E.; Wittmann, S.; Barth, G.; Henle, T. Identification and quantification of methylglyoxal as the dominant antibacterial constituent of Manuka (Leptospermum scoparium) honeys from New Zealand Mol. Nutr. Food Res. 2008, 52, 483-489
3. McLellan, A. C.; Phillips, S. A.; Thornalley, P. J. The assay of methylglyoxal in biological systems by derivatization with 1,2-diamino-4,5- dimethoxybenzene Anal. Biochem. 1992, 206, 17-23
4. Thornalley, P. J.; Langborg, A.; Minhas, H. S. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose Biochem. J. 1999, 344, 109-116
5. Phillips, S. A.; Thornalley, P. J. The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal Eur. J. Biochem. 1993, 212, 101-105
6. Richard, J. P. Kinetic parameters for the elimination reaction catalyzed by triosephosphate isomerase and an estimation of the reactions physiological significance Biochemistry 1991, 30, 4581-4585
7. Thornalley, P. J. Pharmacology of methylglyoxal: Formation, modification of proteins and nucleic acids, and enzymatic detoxification - A role in pathogenesis and antiproliferative chemotherapy Gen. Pharmacol. 1996, 27, 565-573
8. Lyles, G. A.; Chalmers, J. The metabolism of aminoacetone to methylglyoxal by semicarbazide-sensitive amine oxidase in human umbilical artery Biochem. Pharmacol. 1992, 43, 1409-1414
9. --(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins Biochem. J. 1997, 324, 565-570
10. Nagaraj, R. H.; Shipanova, I. N.; Faust, F. M. Protein cross-linking by the Maillard reaction. Isolation, characterization, and in vivo detection of a lysine-lysine cross-link derived from methylglyoxal J. Biol. Chem. 1996, 271, 19338-19345
11. Lederer, M. O.; Klaiber, R. G. Cross-linking of proteins by maillard processes: Characterization and detection of lysine-arginine cross-links derived from glyoxal and methylglyoxal Bioorg. Med. Chem. 1999, 7, 2499-2507
12. Henle, T.; Walter, A. W.; Haessner, R.; Klostermeyer, H. Detection and identification of a protein-bound imidazolone resulting from the reaction of arginine residues and methylglyoxal Z. Lebensm.-Unters. Forsch. 1994, 199, 55-58
13. --(1-carboxyethyl)lysine-modified albumin Biochem. J. 2002, 364, 1-14
14. Oya, T.; Hattori, N.; Mizuno, Y.; Miyata, S.; Maeda, S.; Osawa, T.; Uchida, K. Methylglyoxal modification of protein. Chemical and immunochemical characterization of methylglyoxal-arginine adducts J. Biol. Chem. 1999, 274, 18492-18502
15. Shipanova, I. N.; Glomb, M. A.; Nagaraj, R. H. Protein modification by methylglyoxal: Chemical nature and synthetic mechanism of a major fluorescent adduct Arch. Biochem. Biophys. 1997, 344, 29-36
16. McLellan, A. C.; Thornalley, P. J. Synthesis and chromatography of 1,2-diamino-4,5-dimethoxybenzene, 6,7-dimethoxy-2-methylquinoxaline and 6,7-dimethoxy-2,3-dimethylquinoxaline for use in a liquid chromatographic fluorimetric assay of methylglyoxal Anal. Chim. Acta 1992, 263, 137-142
17. Ahmed, N.; Thornalley, P. J.; Dawczynski, J.; Franke, S.; Strobel, J.; Stein, G.; Haik, G. M. Methylglyoxal-derived hydroimidazolone advanced glycation end-products of human lens proteins Invest. Ophthalmol. Visual Sci. 2003, 44, 5287-5292
18. Gangadhariah, M. H.; Wang, B.; Linetsky, M.; Henning, C.; Spanneberg, R.; Glomb, M. A.; Nagaraj, R. H. Hydroimidazolone modification of human αA-crystallin: Effect on the chaperone function and protein refolding ability Biochim. Biophys. Acta, Mol. Basis Dis. 2010, 1802, 432-441
19. α-(5-Hydroxy- 4,6-dimethylpyrimidine-2-yl)- l -ornithine, a novel methylglyoxal-arginine modification in beer J. Agric. Food Chem. 2001, 49, 366-372
20. Ahmed, N.; Thornalley, P. J. Chromatographic assay of glycation adducts in human serum albumin glycated in vitro by derivatization with 6-aminoquinolyl- N -hydroxysuccinimidyl-carbamate and intrinsic fluorescence Biochem. J. 2002, 364, 15-24
21. Glomb, M. A.; Lang, G. Isolation and characterization of glyoxal-arginine modifications J. Agric. Food Chem. 2001, 49, 1493-1501
22. α- acetyllysine, and bovine serum albumin J. Biol. Chem. 1994, 269, 32299-32305
23. Thornalley, P. J.; Yurek-George, A.; Argirov, O. K. Kinetics and mechanism of the reaction of aminoguanidine with the α-oxoaldehydes glyoxal, methylglyoxal, and 3-deoxyglucosone under physiological conditions Biochem. Pharmacol. 2000, 60, 55-65