Argpyrimidine
chemical compound
Argpyrimidine is an organic compound with the chemical formula C11H18N4O3. It is an advanced glycation end-product formed from arginine and methylglyoxal through the Maillard reaction. Argpyrimidine has been studied for its food chemistry purposes and its potential involvement in aging diseases and diabetes mellitus.
Synthesis
Endogenous
In vivo, argpyrimidine is synthesized from a Methylglyoxal (MG) mediated modification on an arginine residue in a protein. Methylglyoxal is formed through the Polyol pathway, the degradation of triose phosphates from Glycolysis, acetone metabolism, protein Glycation, or Lipid peroxidation. Methylglyoxal then can modify Arginine, Cysteine, or Lysine amino acid residues within a protein. The modification of these side chains through the Maillard reaction forms Advanced glycation end-products (AGEs). This occurs when there is an increase in blood sugar levels in the body. The free sugar compounds undergo alternate pathways, like advanced glycation, to produce AGEs. In the Methylglyoxal-mediated Maillard Reaction on arginine, a dihydroxy-imidazolidine intermediate is involved in the production of the argpyrimidine modification.
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