title: Inhibition of glycosylation processes: the reaction between pyridoxamine and glucose.
abstract: Glycosylation of proteins by glucose produces toxic and immunogenic compounds called 'advanced glycosylation end products' (AGEs), which are the origin of pathological symptoms in various chronic diseases. In this work, a kinetic study of the reaction between glucose (2) and pyridoxamine (1)--a potent inhibitor of AGEs formation both in vivo and in vitro--was conducted. The NH2 group of pyridoxamine was found to react with the C=O group of glucose to form the Schiff base 9 (Scheme 2). Subsequently, the Schiff base gives rise to other products, including compound 3, pyridoxal, pyridoxine, and 4-pyridoxic acid. Compound 3 inhibits the Amadori rearrangement, and prevents the formation of other C=O groups capable of triggering glycosylation processes. Pyridoxal and pyridoxine can also inhibit protein glycosylation via other previously reported mechanisms.
authors.affiliation: Institut Universitari d'Investigació en Ciències de la Salut, Departament de Química, Universitat de les Illes Balears, E-07122 Palma de Mallorca.
authors.forename: Miquel
authors.initials: M
authors.lastname: Adrover
authors.forename: Bartolomé
authors.initials: B
authors.lastname: Vilanova
authors.forename: Francisco
authors.initials: F
authors.lastname: Muñoz
authors.forename: Josefa
authors.initials: J
authors.lastname: Donoso
mesh_terms: D005947:Glucose / Q000737:chemistry*; D017127:Glycation End Products, Advanced / Q000737:chemistry; D006031:Glycosylation; D007700:Kinetics; D015394:Molecular Structure; D011730:Pyridoxal / Q000737:chemistry; D011733:Pyridoxamine / Q000737:chemistry*; D011735:Pyridoxic Acid / Q000737:chemistry; D011736:Pyridoxine / Q000737:chemistry
chemical_list: D017127:Glycation End Products, Advanced; D011730:Pyridoxal; D011735:Pyridoxic Acid; D011733:Pyridoxamine; D005947:Glucose; D011736:Pyridoxine