Formation of a-amino-acid amides and α-hydroxy-acid amides by degradation of sugars with primary amines

Carbohydrate Research

Volumn 300, Issue 3, 1997, Pages 265-269

  Büttner, Ulf ^a   Gerum, Fränzi ^a   Severin, Theodor ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Amino acid amides; Hydroxy acid amides; Cross links; Maillard reaction

Indexed keywords

AMIDE; SUGAR;

ARTICLE; DRUG DEGRADATION; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; MODEL; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0242593405     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(97)00059-1     Document Type: Article

References (23)

1. (a) J.W. Baynes and V.M. Monnier (Eds.), The Maillard Reaction in Aging, Diabetes and Nutrition, Alan R. Liss, New York, 1989;
2. (b) T.B. Labuza, G.A. Reineccius, V.M. Monnier, J. O'Brien, and J.W. Baynes (Eds.), Maillard Reactions in Chemistry, Food, and Health, The Royal Society of Chemistry, Cambridge, 1994.
3. (a) M.U. Ahmed, S.R. Thorpe, and J.W. Baynes, J. Biol. Chem., 261 (1986) 4889-4894;
4. (b) D.V. Zyzac, K.J. Wells-Knecht, J.A. Blackledge, J.E. Lichtfield, M.C. Wells-Knecht, M.-X. Fu, M.S. Feather, and J.W. Baynes, Pathways of the Maillard Reaction In Vitro and In Vivo, in T.B. Labuza, G.A. Reineccius, V.M. Monnier, J. O'Brien, and J.W. Baynes (Eds.), Maillard Reactions in Chemistry, Food, and Health, The Royal Society of Chemistry, Cambridge, 1994, pp 274-280;
5. (c) J. Hartkopf, C. Pahlke, G. Lüdemann, and H.F. Erbersdobler, J. Chromatogr., 672 (1994) 242-246.
6. U. Büttner, S. Ochs, and T. Severin, Carbohydr. Res., 291 (1996) 175-181.
7. J.J. Harding and M.J.C. Crabbe (Eds.), Post-Translational Modifications of Proteins, CRC Press, London, 1992.
8. (a) D.R. Sell and V.M. Monnier, J. Biol. Chem., 264 (1989) 21597-21602;
9. (b) V.M. Monnier and D.R. Sell, The Advanced Maillard Reaction in Aging and Age Related Deseases Probed with Pentosidin, in Maillard Reactions in Chemistry, Food, and Health, T.B. Labuza, G.A. Reineccius, V.M. Monnier, J. O'Brien, and J.W. Baynes, The Royal Society of Chemistry, Cambridge, 1994, pp 235-243.
10. (a) T. Severin and U. Krönig, Z. Lebensm.-Unters. Forsch., 152 (1973) 42-46;
11. (b) F.G. Njoroge, A.A. Fernandes, and V.M. Monnier, J. Carbohydr. Chem., 6 (1987) 553-568;
12. (c) J.G. Farmar, P.C. Ulrich, and A. Cerami, J. Org. Chem., 53 (1988) 2346-2349.
13. (a) M. Sengl, F. Ledl, and T Severin, J. Chromatogr., 463 (1989) 119-125;
14. (b) U. Schüssler and F. Ledl, Z. Lebensm.-Unters. Forsch., 189 (1989) 32-35;
15. (c) F. Hayase, R.H. Nagaraj, S. Miyata, F.G. Njoroge, and V.M. Monnier, J. Biol. Chem., 264 (1989) 3758-3764;
16. (d) T. Henle and H. Klostermeyer, Z. Lebens.-Unters. Forsch., 196 (1993) 1-4.
17. (a) E. Klein, F. Ledl, W. Bergmüller, and T. Severin, Z. Lebensm.-Unters Forsch., 194 (1994) 556-560;
18. (b) R.H. Nagaraj, M. Portero-Otin, and V.M. Monnier, Arch. Biochem. Biophys., 325 (1996) 152-158.
19. J. Nißl, M. Pischetsrieder, E. Klein, and T. Severin, Carbohydr. Res., 270 (1995) C1-C5.
20. M. Friedman, J. Agric. Food. Chem., 44 (1996) 631-653, and literature cited herein.
21. (a) T.W.C. Lo, M.E. Westwood, A.C. McLellan, T. Selwood, and P.J. Thornalley, J. Biol. Chem., 269 (1994) 32299-32305;
22. (b) M.E. Westwood and P.J. Thornalley, J. Protein Chem., 14 (1995) 359-372.
23. K.J. Wells-Knecht, D.V. Zyzak, J.E. Litchfield, S.R. Thorpe, and J.W. Baynes, Biochem., 34 (1995) 3702-3705.