Generation of Proline-Specific Maillard Compounds by the Reaction of 2-Deoxyglucose with Proline

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 8, 1997, Pages 2996-2999

  Chen, Chung Wen ^a   Lu, Guangyuan ^a   Ho, Chi Tang ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

2 deoxyglucose; Aroma generation; Maillard reaction; pH effect; Proline

Indexed keywords

EID: 0344127854     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970197n     Document Type: Article

References (15)

1. Birch, E.; Leliever, J.; Richards, E. L. Thermal analysis of 1-deoxy-1-glycino-D-fructose and 1-β-alanino-1-deoxy-D-fructose. Carbohydr. Res. 1980, 83, 263-272.
2. Helak, B.; Spengler, K.; Tressl, R.; Rewicki, D. Formation of 7H-cyclopen[b]pyridin-7-ones as proline-specific Maillard products. J. Agric. Food Chem. 1989a, 37, 400-404.
3. Helak, B.; Kersten, E.; Spengler, K.; Tressl, R.; Rewicki, D. Formation of furylpyrrolidines and piperidines on heating L-proline with reducing sugars and furancarboxaldehydes. J. Agric. Food Chem. 1989b, 37, 405-410.
4. Huyghues-Despointes, A.; Yaylayan, V. A.; Keyhani, A. Pyrolysis/GC/MS analysis of 1-[(2′-carboxy) pyrrolidinyl]1-deoxy-D-fructose (Proline Amadori compound). J. Agric. Food Chem. 1994, 42, 2519-2524.
5. Lu, G.; Yu, T.-H.; Ho, C.-T. Generation of flavor compounds by the reaction of 2-deoxyglucose with selected amino acids. J. Agric. Food Chem. 1997, 45, 233-236.
6. Mills, F.; Hodge, J. E. Amadori compounds: Vacuum thermolysis of 1-deoxy-1-L-prolino-fructose. Carbohydr. Res. 1976, 51, 9-21.
7. Shigematsu, H.; Shibata, S.; Kurata, T.; Kato, H.; Fujimaki, M. 5-Acetyl-2,3-dihydro-1H-pyrrolizines and 5,6,7,8-tetrahydroindolizin-8-ones. Odor constituents formed on heating L-proline with D-glucose. J. Agric. Food Chem. 1975, 23, 233-237.
8. Tressl, R.; Grunewald, K. G.; Halek, B. Formation of flavor components from proline and hydroxyproline with glucose and maltose and their importance to food flavor. In Flavor '81; Schreier, P., Ed.; Walter de Gruyter Co.: Berlin, 1981; pp 397-416.
9. Tressl, R.; Rewicki, D.; Helak, B.; Kamperschroer, H.; Martin, N. Formation of 2,3-dihydro-1H-pyrrolizines as proline specific Maillard products. J. Agric. Food Chem. 1985a, 33, 919-923.
10. Tressl, R.; Rewicki, D.; Helak, B.; Kamperschroer, H. Formation of pyrrolidines and piperidines on heating L-proline with reducing sugars. J. Agric. Food Chem. 1985b, 33, 924-928.
11. Tressl, R.; Helak, B.; Koppler, H.; Rewicki, D.; Formation of 2-(1-pyrrolidinyl)-2-cyclopentenones and cyclopent[b]azepines as proline specific Maillard products. J. Agric. Food Chem. 1985c, 33, 1132-1137.
12. 13C] glucose. J. Agric. Food Chem. 1993, 41, 547-553.
13. Vernin, G.; Debrauwer, L.; Vermin, G. M. F.; Zamkotsian, R.-M.; Metzger, J.; Larice, J. L.; Parkanyi, C. Heterocycles by thermal degradation of Amadori intermediates. In Off-Flavours in Foods and Beverages, Charalambous, G., Ed.; Elsevier Science Publishers: Amsterdam, 1992a; pp 567-621.
14. Vernin, G.; Metzger, J.; Boniface, C.; Murello, M.-H.; Siouffi, A.; Larice, J.-L.; Parkayi, C. Kinetics and thermal degradation of the methionine Amadori intermediates, GC-MS/ SPECMA data bank identification of volatile aroma compounds. Carbohydr. Res. 1992b, 230, 15-29.
15. Whistler, R. L.; Daniel, J. R. Carbohydrates. In Food Chemistry, Fennema, O. R., Ed.; Marcel Dekker, Inc.: New York, 1985; pp 69-137.