glucosepane
Sign in to saveGlucosepane is a lysine-arginine protein cross-linking product and advanced glycation end product (AGE) derived from D-glucose. It is an irreversible, covalent cross-link product that has been found to make intermolecular and intramolecular cross-links in the collagen of the extracellular matrix (ECM) and crystallin of the eyes. Covalent protein cross-links irreversibly link proteins together in the ECM of tissues. Glucosepane is present in human tissues at levels 10 to 1000 times higher than any other cross-linking AGE, and is currently considered to be the most important cross-linking AGE.
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 428.23833274399993
Show 4 more facts
- canonical SMILES
- C1C(C(CN(C2=NC(=NC12)NCCCC(C(=O)O[H])N)CCCCC(C(=O)O[H])N)O[H])O[H]
- density
- 1.6
- chemical formula
- C₁₈H₃₂N₆O₆
- isomeric SMILES
- N[C@@H](CCCCN1C[C@@H](O)[C@@H](O)CC2NC(=NCCC[C@H](N)C(=O)O)N=C21)C(=O)O
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Encyclopedic overview
13 sectionsContents
- Role in aging
- Formation
- Overall reaction pathway
- Mechanism of α-dicarbonyl formation from the Amadori product
- Ring closure to arginine cross-linking
- Accumulation
- Detection
- Prospects for inhibition or removal
- α-Dicarbonyl trap
- Thiazolium salts
- ECM turnover
- See also
- References
Glucosepane is a lysine-arginine protein cross-linking product and advanced glycation end product (AGE) derived from D-glucose. It is an irreversible, covalent cross-link product that has been found to make intermolecular and intramolecular cross-links in the collagen of the extracellular matrix (ECM) and crystallin of the eyes. Covalent protein cross-links irreversibly link proteins together in the ECM of tissues. Glucosepane is present in human tissues at levels 10 to 1000 times higher than any other cross-linking AGE, and is currently considered to be the most important cross-linking AGE.
== Role in aging ==
Excerpted from Wikipedia’s “glucosepane” article, available under the CC BY-SA 4.0 licence.