Formation of pyrazines in hydroxyacetaldehyde and glycine nonenzymatic browning Maillard reaction: A computational study

Food Chemistry

Volumn 103, Issue 4, 2007, Pages 1208-1216

  Jalbout, Abraham F ^a   Shipar, Md Abul Haider ^b  

^a UNIVERSITY OF ARIZONA   (United States)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Density functional theory computation; Glycine; Hydroxyacetaldehyde; Nonenzymatic browning Maillard reaction; Pyrazines

Indexed keywords

2,3,5,6 TETRAHYDROPYRAZINE; 3,6 DIHYDROPYRAZINE; ACETALDEHYDE; GLYCINE; GLYCOLALDEHYDE; GLYOXAL; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; DENSITY FUNCTIONAL THEORY; FEASIBILITY STUDY; GAS; GLYCATION; ISOELECTRIC POINT; PH;

EID: 33947504728     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2006.10.025     Document Type: Article

References (47)

1. Akhand A.A., Hossain K., Kato M., Miyata T., Du J., Suzuki H., et al. Glyoxal and methylglyoxal induce lyoxal and methyglyoxal induce aggregation and inactivation of ERK in human endothelial cells. Free Radical Biology and Medicine 31 (2001) 1228-1235
2. Ames J.M. Control of the Maillard reaction in food systems. Trends in Food Science and Technology 1 (1990) 150-154
3. Bell L.N. Maillard reaction as influenced by buffer type and concentration. Food Chemistry 59 (1997) 143-147
4. Bjeldanes L.F., and Chew H. Mutagenicity of 1,2-dicarbonyl compounds: Maltol, kojic acid, diacetyl and related substances. Mutation Research 67 (1979) 367-371
5. Bulat F., and Toro-Labbé A. A theoretical study of the rotational isomerization of glyoxal and halogen derivatives. Chemical Physics Letters 354 (2002) 508-517
6. Davdeḱ J., Velśek J., and Pokorný J. Development in food science: Chemical changes during food processing Vol. 21 (1990), Elsevier Science Publishers, Amsterdam 117-152
7. Eskin N.A.E. Biochemistry of foods. (2nd ed., pp. 239-296) (1990), Academic Press, San Diego
8. Foresman J.B., and Frisch A. Exploring chemistry with electronic structure methods. 2nd ed. (1996), Gaussian, Inc., Pittsburgh, USA
9. Frisch Æ., and Foresman J.B. Gaussian 98 user's reference (1998), Gaussian, Inc., Pittsburg, USA
10. Harrold H. Organic chemistry: A short course. (8th ed., pp. 425-467) (1991), Houghton Mifelin Company, Boston
11. Hayashi T., and Namiki M. Role of sugar fragmentation: An early stage browning of amino-carbonyl reaction of sugar and amino acid. Agriculture and Biological Chemistry 50 (1986) 1965-1970
12. Hehre W.J., Radom L., Schleyer P.V.R., and Pople J.A. Ab initio molecular orbital theory (1986), John Wiley & Sons, New York
13. Ho C.T., and Chen J. Generation of volatile compounds from Maillard reaction of serine, threonine, and glutamine with monosaccharides. In: Teranishi R., Wick E.L., and Hornstein I. (Eds). Flavour chemistry: Thirty years of progress (1999), Kluwer Academic and Plenum Publishers, New York 327-334
14. Hodge J.E. Chemistry of browning reactions in model systems. Journal of Agricultural and Food Chemistry 1 (1953) 928-943
15. Holum J.R. Introduction to organic and biological chemistry. (pp. 196-204) (1996), John Wiley & Sons, New York
16. Labuza T.P., and Saltmarch M. The nonenzymatic browning reaction as affected by water in foods. In: Rockland L.B., and Stewart B.S. (Eds). Water activity influences food quality (1981), Academic Press, New York 605-639
17. Lea C.H., and Hannan R.S. Studies of the reaction between proteins and reducing sugars in the dry state I, the effect of activity of water, of pH and of temperature on the primary reaction between casein and glucose. Biochimica et Biophysica Acta 3 (1949) 313-325
18. Ledl F., and Schleicher E. New aspects of the Maillard reaction in foods and in the human body. Angewandte Chemie International Edition in English 29 (1990) 565-594
19. Leng F., Graves D., and Chaires J.B. Chemical cross-linking of ethidium to DNA by glyoxal. Biochimica et Biophysica Acta 1442 (1998) 71-81
20. Macrane R., Robinson R.K., and Saadler M.J. Encyclopedia of food science, food technology and nutrition vol. 1 (1993), Academic Press Limited, London 146-166
21. Maillard L.C. Action des acides aminés sur les sucres: Formation des mélanoides par voi méthodique. Comptes Rendus de l Academie des Sciences Serie 145 (1912) 66-68
22. Meade S.J., Miller A.G., and Gerrard J.A. The role of dicarbonyl compounds in non-enzymatic crosslinking: a structure activity study. Bioorganic & Medicinal Chemistry 11 (2003) 853-862
23. Mistry N., Evans M.D., Griffiths H.R., Kasai H., Herbert K.E., and Lunec J. Immunochemical detection of glyoxal DNA damage. Free Radical Biology and Medicine 26 (1999) 1267-1273
24. Moree-Testa P., and Saint-Jalm Y. Determination of α-dicarbonyl compounds in cigarette smoke. Journal of Chromatography 217 (1981) 197-208
25. Murata-Kamiya N., Kamiya H., Kaji H., and Kasai H. Biochemical and Biophysical Research Communications 248 (1998) 412-417
26. Namiki M., and Hayashi T. A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation. In: Waller G.R., and Feather M.S. (Eds). The Maillard reaction in foods and nutrition. American Chemical Society symposium series Vol. 215 (1983), American Chemical Society, Washington, DC 1-46
27. Nursten H.E. Maillard browning reactions in dried foods. In: MacCarthy D. (Ed). Concentration and drying of foods (1986), Elsevier Applied Science, London 53-58
28. 13C)-d-glucose and glycine. In: Waller G.R., and Feather M.S. (Eds). The Maillard reaction in foods and nutrition. American Chemical Society Symposium Series Vol. 215 (1983), American Chemical Society, Washington, DC 71-82
29. Odani H., Shinzato T., Matsumoto Y., Usami J., and Maeda K. Increase in three α,β-dicarbonyl compound levels in human uremic plasma: specific in vivo determination of intermediates in advanced Maillard reaction. Biochemical and Biophysical Research Communications 256 (1999) 89-93
30. Odani H., Shinzato T., Usami J., Matsumoto Y., Frye E.B., Baynes J.W., et al. Imidazolium crosslinks derived from reaction of lysine with glyoxal and methylglyoxal are increased in serum proteins of uremic patients: evidence for increased oxidative stress in uremia. FEBS Letters 427 (1998) 381-385
31. Reber F., Kasper M., Siegner A., Kniep E., Seigel G., and Funk R.H.W. Alteration of the intracellular pH and apoptosis induction in a retinal cell line by the AGE-inducing agent glyoxal. Graefe's Archive for Clinical and Experimental Ophthalmology 240 (2002) 1022-1032
32. Sady C., Jiang C.L., Chellan P., Madhun Z., Duve Y., Glomb M.A., et al. Maillard reactions by α-oxoaldehydes: detection of glyoxal-modified proteins. Biochimica et Biophysica Acta 1481 (2000) 255-264
33. Sancho-García J.C., Peréz-Jiménez A.J., Pérez-Jordá J.M., and Moscardó F. High-level ab initio calculations of the torsional potential of glyoxal. Chemical Physics Letters 342 (2001) 452-460
34. Sayato Y., Nakamuro K., and Ueno H. Mutagenicity of products formed by ozonation of naphthoresorcinol in aqueous solutions. Mutation Research 189 (1987) 217-222
35. Shangari N., and O'Brien P.J. The cytotoxic mechanism of glyoxal involves oxidative stress. Biochemical Pharmacology 68 (2004) 1433-1442
36. Shibamoto T., and Bernhard R.A. Formation of heterocyclic compounds from the reaction of l-rhamnose with ammonia. Journal of Agricultural and Food Chemistry 26 (1978) 183-187
37. Shipar M.A.H. Computational studies on glyceraldehyde and glycine Maillard reaction - III. Journal of Molecular Structure - Theochem 712 (2004) 39-47
38. Shipar M.A.H. Formation of pyrazines in dihydroxyacetone and glycine Maillard reaction: a computational study. Food Chemistry 98 (2006) 403-415
39. Shipar, M. A. H., Jalbout, A. F., & Adamowicz, L. (submitted for publication). Formation of glyoxal in hydroxyacetaldehyde and glycine nonenzymatic browning Maillard reaction: a computational study. Food Chemistry.
40. Shu C.K. Pyrazine formation from serine and threonine. Journal of Agricultural and Food Chemistry 47 (1999) 4332-4335
41. Tantirungrotechai Y. Effect of an external electric field and a neighbouring atom on the torsional potential of glyoxal: a computational study. Journal of Molecular Structure - Theochem 624 (2003) 279-286
42. Thornalley P.J., George A.Y., and Argirov O.K. Kinetics and mechanism of the reaction of aminoguanidine with the α-oxoaldehydes glyoxal, methylglyoxal, and 3-deoxyglucosone under physiological conditions. Biochemical Pharmacology 60 (2000) 55-65
43. 13C]-D-fructose. Journal of Agricultural and Food Chemistry 43 (1995) 1163-1169
44. Wilen S.H. Synthesis and properties of 2,5-dihydro-3,6-dimethylpyrazine. Journal of Chemical Society D: Chemical Communication 1 (1970) 25-26
45. Wong J.W., and Shibamoto T. Genotoxicity of Maillard reaction products. In: Ikan R. (Ed). The Maillard reaction: consequences for the chemical and life sciences (1996), John Wiley & Sons, Ltd., Chichester, West Sussex, England, New York 129-160
46. Young D.C. Computational chemistry: A practical guide for applying techniques to real world problems (2001), John Wiley & Sons, New York
47. u) states of the glyoxal molecule. Computers and Chemistry 24 (2000) 263-274