3-deoxyglucosone

3-Deoxyglucosone

Names
IUPAC name (4S,5R)-4,5,6-Trihydroxy-2-oxohexanal
Other names 3-Deoxy-D-erythro-hexosulose; 2-Keto-3-deoxyglucose; 3-Deoxy-D-erythro-hexos-2-ulose; 3-Deoxy-D-erythro-hexosulose; 3-Deoxy-D-glucosone; D-3-Deoxyglucosone
Identifiers
CAS Number	4084-27-9 N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:60777 Y
ChemSpider	102799 Y
PubChem CID	114839
InChI InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1 Y Key: ZGCHLOWZNKRZSN-NTSWFWBYSA-N Y InChI=1/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1 Key: ZGCHLOWZNKRZSN-NTSWFWBYBM
SMILES C(C(C(CO)O)O)C(=O)C=O O=C(C=O)C[C@H](O)[C@H](O)CO
Properties
Chemical formula	C6H10O5
Molar mass	162.14 g·mol−1
Density	1.406 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

3-Deoxyglucosone (3DG) is a dicarbonyl sugar that is synthesized through the Maillard reaction, and is metabolized to 3-deoxyfructose and 2-keto-3-deoxygluconic acid. 3DG is a precursor for the formation of advanced glycation end-products (AGEs): 3DG rapidly reacts with protein amino groups to form AGEs such as imidazolone, pyrraline, N⁶-(carboxymethyl)lysine, and pentosidine. 3DG as well as AGEs play a role in the modification and cross-linking of long-lived proteins such as crystallin and collagen, contributing to diseases such as the vascular complications of diabetes, atherosclerosis, hypertension, Alzheimer's disease, inflammation, and aging.

3DG is a highly reactive sugar that is found in high-fructose corn syrup and in many foods. It is also made naturally by the body when excessive sugar is consumed or when a person is diabetic. Glucose reacts non-enzymatically with protein amino groups to initiate glycation, the early stage of the Maillard reaction. In the intermediate and late stages of glycation, the spontaneous formation of highly reactive compounds such as 3DG may account for the numerous features of diabetic complication as well as aging.

In 1990, the Brown group from Fox Chase Cancer Center in Philadelphia identified fructose 3-phosphate (F3P) in lenses from diabetic rats. This shows the existence of the only mammalian kinase that phosphorylates a sugar on a secondary hydroxyl group. F3P is an unstable compound, and the spontaneous decomposition of F3P leads to formation of 3DG. In 2000, the 3-phosphokinase responsible for the formation of F3P was cloned and named fructosamine 3-kinase (FN3K).