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Elucidation of Chemical Pathways in the Maillard Reaction by 17 O‐NMR Spectroscopy
Author(s) -
ROBERT FABIEN,
VERA FRANCIA ARCE,
KERVELLA FRANK,
DAVIDEK TOMAS,
BLANK IMRE
Publication year - 2005
Publication title -
annals of the new york academy of sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.712
H-Index - 248
eISSN - 1749-6632
pISSN - 0077-8923
DOI - 10.1196/annals.1333.008
Subject(s) - maillard reaction , chemistry , acetic acid , nuclear magnetic resonance spectroscopy , sugar , spectroscopy , fragmentation (computing) , mass spectrometry , diastereomer , organic chemistry , stereochemistry , chromatography , physics , quantum mechanics , computer science , operating system
A bstract :17 O‐NMR spectroscopy was employed as an innovative method to help understand mechanistic pathways in sugar fragmentation. Elucidation of reaction mechanisms to final Maillard end products was achieved by starting from specific intermediates obtained by synthesis, such as 1‐deoxy‐d‐ erythro ‐hexo‐2,3‐diulose. This α‐dicabonyl was thermally treated in the presence of 17 O‐enriched water under alkaline conditions. The reaction products were monitored by 17 O‐NMR spectroscopy and their structures corroborated by complementary techniques. For the first time, evidence is shown for the direct formation of acetic acid from 1‐deoxy‐d‐ erythro ‐hexo‐2,3‐diulose by an oxidative α‐dicarbonyl cleavage and incorporation of a 17 OH group into the acetic acid released as sugar fragment.