Synthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate.
1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythronolactone derivative. Characterization by 1H and 13C NMR spectroscopy and NOE difference experiments revealed the 2C5-chair beta-pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved 1-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose.
Glomb
M A
MA
Institute of Food Chemistry, Technical University of Berlin, Germany. glom1530@mailszrz.zrz.tu-berlin.de
Pfahler
C
C
D005504:Food Analysis; D007661:Ketoses / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D011506:Proteins / Q000737:chemistry
C421122:1-deoxy-erythro-hexo-2,3-diulose; D007661:Ketoses; D011506:Proteins