4084-27-9

Amorphous Yellow Solid

An intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. An intermediate in the formation of pyrraline, which might contribute to a pathological effect, such as carcinogenesis

ChEBI: A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.

3-deoxy Glucosone is a highly reactive 2-oxoaldehyde intermediate of the Maillard reaction produced during oxidative stress in response to excess sugar consumption and in association with diabetes. It is a precursor for the formation of advanced glycation endproducts and because it readily reacts with protein amino groups is also used for crosslinking studies. 3-deoxy Glucosone can be used as a reference for the analysis and detection of glucose degradation products and glycating agents.

[1] H YAMADA. Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction.[J]. The Journal of Biological Chemistry, 1994, 269 32: 20275-20280.
[2] HITOMI KUSUNOKI. Relation between serum 3-deoxyglucosone and development of diabetic microangiopathy.[J]. Diabetes Care, 2003, 26 6: 1889-1894. DOI: 10.2337/diacare.26.6.1889
[3] TOSHIMITSU NIWA  Saori T. 3-Deoxyglucosone and AGEs in uremic complications: Inactivation of glutathione peroxidase by 3-deoxyglucosone[J]. Kidney international, 2001, 59: Pages S37-S41. DOI: 10.1046/j.1523-1755.2001.59780037.x
[4] PAUL J THORNALLEY H M A Langborg. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose.[J]. The Ukrainian Biochemical Journal, 1999, 16 1: 109-116. DOI: 10.1042/bj3440109