title: Interaction of free arginine and guanidine with glucose under thermal processing conditions and formation of Amadori-derived imidazolones.
abstract: To investigate the reactivity of free guanidine and arginine in the formation of imidazolinone derivatives, model systems of guanidine or arginine/glucose or13[C-6]-glucose were heated in aqueous solutions at110°C for 3h and the residues were analyzed by ESI/qTOF/MS using MS/MS and isotope labeling techniques. The analysis of the data indicated that guanidine and arginine formed both covalent and non-covalent interaction products. Covalent interactions included Amadori rearrangement at the α-nitrogen with glucose and imidazolinone formation with 3-deoxy-glucosone at the guanidine side-chain. Non-covalent interactions, such as self-interaction and interaction with free guanidine or arginine and glucose, were also observed. Guanidine underwent three sequential Amadori rearrangements and the free and mono-glycated guanidine also formed imidazolinone derivatives and their corresponding dehydration products and at the same time exhibiting various non-covalent interactions. On the other hand, arginine formed free Amadori product, free imidazolinone and Amadori-derived imidazolinone derivative in addition to methylglyoxal-derived hydroimidazolones.
authors.affiliation: Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec H9X 3V9, Canada.
authors.forename: Yuchen
authors.initials: Y
authors.lastname: Zhu
authors.affiliation: Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec H9X 3V9, Canada. Electronic address: varoujan.yaylayan@mcgill.ca.
authors.forename: Varoujan A
authors.initials: VA
authors.lastname: Yaylayan
mesh_terms: D001120:Arginine / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D019791:Guanidine / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D011765:Pyruvaldehyde / Q000737:chemistry; D053719:Tandem Mass Spectrometry
chemical_list: D007093:Imidazoles; C117197:imidazolone; D011765:Pyruvaldehyde; D001120:Arginine; D005947:Glucose; D019791:Guanidine
keywords: 1,2-Dicarbonyls; Amadori product; Arginine; Glucose; Guanidine; Imidazolinone