Identification of 3,4-dihydroxy-2-oxo-butanal (L-threosone) as an intermediate compound in oxidative degradation of dehydro-L-ascorbic acid and 2,3-diketo-L-gulonic acid in a deuterium oxide phosphate buffer.
Dehydro-L-ascorbic acid (DAA), an oxidation product of L-ascorbic acid (vitamin C), is unstable in the neutral and basic pH regions. When DAA was incubated in a phosphate buffer with deuterium oxide (pH 7.4), it was degraded to form the main degradation compound, which was identified as 3,4-dihydroxy-2-oxobutanal (L-threosone). This compound was also formed from diketo-L-gulonic acid (DKG) in a phosphate buffer with deuterium oxide. L-threosone had reducing activity, probably due to its enolization, and is likely to have been involved in the formation of the reducing activity that was observed in aqueous DAA and DKG solutions. As a reactive dicarbonyl compound, L-threosone might also take some role in the cross-linking of tissue proteins that are formed in vivo in the Maillard reaction.
Nishikawa
Y
Y
Institute of Environmental Science for Human Life, Ochanomizu University, Tokyo, Japan. n-yoko@cc.ocha.ac.jp
Toyoshima
Y
Y
Kurata
T
T
D015083:2,3-Diketogulonic Acid / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002021:Buffers; D002853:Chromatography, Liquid; D003683:Dehydroascorbic Acid / Q000737:chemistry*; D017666:Deuterium Oxide / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008970:Molecular Weight; D019815:Oxalic Acid / Q000737:chemistry; D010084:Oxidation-Reduction; D010710:Phosphates; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet
C448739:3,4-dihydroxy-2-oxo-butanal; D000447:Aldehydes; D002021:Buffers; D006835:Hydrazones; D010710:Phosphates; D015083:2,3-Diketogulonic Acid; D019815:Oxalic Acid; D017666:Deuterium Oxide; D003683:Dehydroascorbic Acid