Structure determination of a novel 3(6H)-pyranone chromophore and clarification of its formation from carbohydrates and primary amino acids

Citation
O. Frank et al., Structure determination of a novel 3(6H)-pyranone chromophore and clarification of its formation from carbohydrates and primary amino acids, J AGR FOOD, 49(3), 2001, pp. 1595-1600
Citations number
11
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis
Journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN journal
0021-8561 → ACNP
Volume
49
Issue
3
Year of publication
2001
Pages
1595 - 1600
Database
ISI
SICI code
0021-8561(200103)49:3<1595:SDOAN3>2.0.ZU;2-3
Abstract
An intensely orange compound, which has recently been evaluated as one of t he main colored compounds formed in Maillard reactions of hexoses, could be unequivocally identified as (Z)-2-[(2-furyl)methylidene] -5,6-di(2-furyl)- 6H-pyran-3-one (1) by application of several NMR and LC-MS experiments. To clarify its formation, the effectiveness of certain carbohydrate degradatio n products as precursors of 1 was studied in a quantitative experiment demo nstrating hydroxy-2-propanone, furan-2-aldehyde, and 3-deoxy-2-hexosulose a s precursors of the colorant. Site-specific labeling experiments with D-1-[ C-13]glucose and D-6-[C-13]glucose, respectively, were performed to elucida te the formation pathway of 1 involving a cleavage of the hexose skeleton b etween carbon atoms C(5) and C(6). In addition, pentoses could be shown to generate 1 via a similar formation pathway involving the 3-deoxy-2-pentosul ose.