17678-20-5Relevant articles and documents
DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine
Hiramoto, Kazuyuki,Nasuhara, Akiko,Michikoshi, Kae,Kato, Tetsuta,Kikugawa, Kiyomi
, p. 47 - 56 (1997)
Aqueous solution of glucose and glycine was heated under reflux for 4 h and extracted with ethyl acetate. Reversed phase HPLC of the extract revealed a new DNA strand-breaking substance, which was purified by repeated HPLC and identified as 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP). DDMP induced DNA strand breaking in a dose- and time-dependent manner. It was active to break DNA strands at pH 7.4 and 9.4. Its pyranone skeleton was destroyed at the pH values. DNA strand breaking by DDMP was inhibited by superoxide dismutase, catalase, scavengers for hydroxyl radical, spin trapping agents and metal chelators, and the breaking was enhanced by Fe(III) ion. A mixture of DDMP and a spin trap DMPO gave electron spin resonance signals of a spin adduct DMPO-OH, indicating generation of hydroxyl radical. DDMP was found to be mutagenic to Salmonella typhimurium TA100 without metabolic activation. These results show DDMP generated active oxygen species to cause DNA strand breaking and mutagenesis.
Oxygen-dependent fragmentation reactions during the degradation of 1-deoxy-d-erythro-hexo-2,3-diulose
Voigt, Michael,Smuda, Mareen,Pfahler, Christoph,Glomb, Marcus A.
experimental part, p. 5685 - 5691 (2011/08/05)
With this work, we report on further insights into the chemistry of 1-deoxy-d-erythro-hexo-2,3-diulose (1-deoxyglucosone, 1-DG). This α-dicarbonyl plays an important role as a highly reactive intermediate in the Maillard chemistry of hexoses. Degradation of 1-DG in the presence of the amino acid l-alanine led to the formation of several products. Lactic acid and glyceric acid were found to be major degradation products. Their formation was dependent on the presence of oxygen. Therefore, a mechanism is postulated based on oxidation leading to a tricarbonyl intermediate. Carbonyl cleavage of this structure should then give rise to carboxylic acids. This mechanism was supported by the isotope distribution observed during degradation of different 13C-labeled d-glucose isotopomers. Furthermore, we identified 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (γ-pyranone) to be capable of rehydration forming 1-DG to a minor extent and therefore leading to the same degradation products. The formation of carboxylic acids from γ-pyranone was also dependent on the presence of oxygen in agreement with the postulated oxidative fragmentation. Finally, we investigated the formation of aldehydes expected as retro-aldol products formed within the degradation of 1-DG. Results seemed to rule out this reaction as an important degradation pathway under the conditions investigated herein.
SYNTHESIS OF A DERIVATIVE OF 1-DEOXY-D-erythro-2,3-HEXODIULOSE AND ITS CONVERSION INTO NONENZYMIC BROWNING PRODUCTS
Fisher, Benjamin E.,Sinclair, Henry B.,Goodwin, James C.
, p. 209 - 216 (2007/10/02)
A new synthesis of 1-deoxy-4,5-O-isopropylidene-D-erythro-2,3-hexodiulose (5), a stable derivative of the elusive 1-deoxy-D-erythro-2,3-hexodiulose (6), starting from 3,6-anhydro-4,5-O-isopropylidene-D-mannitol (1) is described.Acid hydrolysis of 5 produced 6, which without isolation was treated with piperidine acetate to yield piperidino-hexose-reductone (7) and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (8).A third component in the reaction mixture has been tentatively assigned from mass-spectroscopic data the structure 4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone (9).
