Vinylogous Amadori rearrangement: Implications in food and biological systems

Molecular Nutrition and Food Research

Volumn 51, Issue 4, 2007, Pages 437-444

  Yaylayan, Varoujan A ^a,b   Locas, Carolina P ^a  

^a MCGILL UNIVERSITY   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

2 deoxy sugars; 4 hydroxy 2 alkenals; Amadori rearrangement; FTIR; Protein damage

Indexed keywords

4 HYDROXYNONENAL; 4-HYDROXY-2-NONENAL; ALDEHYDE; AMINO ACID; DEOXYRIBOSE; PROLINE; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ARTICLE; CHEMISTRY; CYCLIZATION; FOOD ANALYSIS; GLYCATION; INFRARED SPECTROSCOPY; LIPID PEROXIDATION; OXIDATION REDUCTION REACTION; PHYSICAL CHEMISTRY;

ALDEHYDES; AMINO ACIDS; CHEMISTRY, PHYSICAL; CYCLIZATION; DEOXYRIBOSE; FATTY ACIDS, UNSATURATED; FOOD ANALYSIS; LIPID PEROXIDATION; MAILLARD REACTION; OXIDATION-REDUCTION; PROLINE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 34447512796     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.200600126     Document Type: Conference Paper

References (22)

1. Golubev, A. G., The other side of metabolism: A review, Biochemistry (Moscow) 1996, 61, 1443-1460.
2. Yin, D., Chen, K., The essential mechanisms of aging: Irreparable damage accumulation of biochemical side-reactions, Exp. Gerentol., 2005, 40, 455-465.
3. Yaylayan, V. A., Huyghues Despointes, A., Chemistry of Amadori rearrangement products: Analysis, synthesis, kinetics, reactions and spectroscopic properties, Crit. Rev. Food Sci. Nutr. 1994, 34, 321-369.
4. Henle, T., Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in food, Amino acids 2005, 29, 313-322.
5. Baynes, J. W., Chemical modification of proteins by lipids in diabetes, Clin. Chem Lab Med. 2003, 41, 1159-1165.
6. Monnier, V. M., Intervention against the Maillard reaction in vivo, Arch. Biochem. Biophys. 2003, 419, 1-15.
7. Manini, P., Napolitano, A., d'Ischia, M., Reactions of D-glucose with phenolic amino acids: Further insights into the competition between Maillard and Pictet-Spengler condensation pathways, Carbohydr. Res. 2005, 340, 2719-2727.
8. Yaylayan, V., Pare, J. R. J., Laing, R., Sporns, P., Formation of β-carbolines from 1-[(1′-carboxy-2′-indol-3′-yl-ethyl) amino]-1-deoxy-D-fructose under electron impact conditions, Org. Mass Spectrom. 1990, 25, 141-145.
9. Zamaro, R., Hidalgo, F. J., Coordinate contribution of lipid oxidation and maillard reaction to the nonenzymatic food browning, Crit. Rev. Food Sci. Nutr. 2005, 45, 49-59.
10. Lambert, J. B., Shurvell, H. F., Lighner, D. A., Cooks, R. G., "Organic Structural Spectroscopy", Prentive-Hall Inc, New Jersey 1998.
11. Xu, G, Sayer, L. M., Structural characterization of a 4-hydroxy-2-nonenal-derived fluorophore that contributes to lipoperoxidation- dependent protein cross-linking in aging and degenerative disease, Chem. Res. Toxicol. 1998, 11, 247-251.
12. Vichi, S., Pizzale, L., Conte, L. S., Buxaderas, S., López- Tamames, E., J.Agric. Food Chem. 2003, 51, 6564-6571.
13. Hidalgo, F. J., Zamora, R., Strecker-type degradation produced by the lipid oxidation products 4,5-epoxy-2-alkenals, J. Agric. Food Chem. 2004, 52, 7126-7131.
14. Hidalgo, F. J., Gallardo, E., Zamora, R., Strecker type degradation of phenylalanine by 4-hydroxy-2-nonenal in model systems, J. Agric. Food Chem. 2005, 53, 10254-10259.
15. Esterbauer, H., Schaur, R. J., Zollner, H., Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes, Free Radic. Biol. Med. 1991, 11, 81-128.
16. Benedetti, A., Comporti, M., Esterbauer, H., Identification of 4-hydroxynonenal as a cytotoxic product originating from the peroxidation of liver microsomal lipids, Biochim. Biophys. Acta 1980, 620, 281-296.
17. Sayre, L. M., Guozhang, W. S., Kaur, K., Nadkarni, D. et al., Immunochemical evidence supporting 2-pentylpyrrole formation on proteins exposed to 4-hydroxy-2-nonenal, Chem. Res. Toxicol. 1993, 9, 1194-1201.
18. Sayre, L. M., Arora, P. K., Iyer, R. S., Salomon, R. G., Pyrrole formation from 4-hydroxynonenal and primary amines, Chem. Res. Toxicol. 1993, 9, 19-22.
19. Wondrak, G. T., Tressl, R., Rewicki, D., Maillard reaction of free and nucleic acid bound 2-deoxy-D-ribose and D-ribose with ω-amino acids, J. Agric. Food Chem. 1997, 45, 321-327.
20. Perez Locas, C., Yaylayan, V., Origin and mechanistic pathways of formation of the parent furan - A food toxicant, J. Agric. Food Chem. 2004, 52, 6830-6836.
21. Nelsestuen, G. L., Amino acid catalyzed condensation of purines and pyrimidines with 2-deoxy-ribose, Biochemistry, 1979, 18, 2843-2846.
22. Yaylayan, V., Precursors, formation and determination of furan in food, J. Verbr. Lebensm. 2006, 1, 5-9.