Structure via PubChem · Public domain (PubChem)
3-deoxyglucosone
Sign in to saveAlso known as 3-Deoxy-D-glucosone, 3-deoxy-D-erythro-hexosulose, 3-deoxy-2-ketoglucose, 3-deoxy-D-erythro-hexulose, 3-deoxy-D-fructose, 3-deoxy-erythro-hexos-2-ulose
3-Deoxyglucosone (3DG) is a sugar that is notable because it is a marker for diabetes. 3DG reacts with protein to form advanced glycation end-products (AGEs), which contribute to diseases such as the vascular complications of diabetes, atherosclerosis, hypertension, Alzheimer's disease, inflammation, and aging.
In the Vinony graph
Within Vinony's link graph, 3-deoxyglucosone is referenced by 7 other articles, and connects out to atherosclerosis, diabetes and International Standard Book Number.
Vinony files it under Advanced glycation end-products, Chembox image size set and Chemical articles with multiple compound IDs.
Its subject is documented across 5 Wikipedia language editions.
Chemical data
- Formula
- C6H10O5
- Molecular weight
- 162.14 g/mol
- IUPAC name
- (4S,5R)-4,5,6-trihydroxy-2-oxohexanal
- SMILES
- C([C@@H]([C@@H](CO)O)O)C(=O)C=O
- InChIKey
- ZGCHLOWZNKRZSN-NTSWFWBYSA-N
- XLogP
- -2.4
- Polar surface area
- 94.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 162.052823
Show 3 more facts
- canonical SMILES
- C(C(C(CO)O)O)C(=O)C=O
- chemical formula
- C₆H₁₀O₅
- isomeric SMILES
- C([C@@H]([C@@H](CO)O)O)C(=O)C=O
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- Biosynthesis
- Biochemistry
- 3DG and ROS
- Detoxification
- Additional reading
- References
3-Deoxyglucosone (3DG) is a sugar that is notable because it is a marker for diabetes. 3DG reacts with protein to form advanced glycation end-products (AGEs), which contribute to diseases such as the vascular complications of diabetes, atherosclerosis, hypertension, Alzheimer's disease, inflammation, and aging.
==Biosynthesis== thumb|left|4-Imidazolone arise from the condensation of arginine residues and 3-deoxyglucosone (R = CH2CH(OH)CH(OH)CH2OH). 3DG is made naturally via the Maillard reaction. It forms after glucose reacts with primary amino groups of lysine or arginine found in proteins. Because of the increased concentration of the reactant glucose, more 3DG forms with excessive blood sugar levels, as in uncontrolled diabetes. Glucose reacts non-enzymatically with protein amino groups to initiate glycation. The formation of 3DG may account for the numerous complications of diabetes as well as aging.
Excerpted from Wikipedia’s “3-deoxyglucosone” article, available under the CC BY-SA 4.0 licence.