title: Conversion of Amadori product of Maillard reaction to Nepsilon-(carboxymethyl)lysine in alkaline condition.
abstract: Nepsilon-(carboxymethyl)lysine (CML) is known to be formed by oxidative cleavage of Amadori products between C-2 and C-3 of the carbohydrate chain. We report here that CML formation from Amadori compounds is highly accelerated under alkaline conditions. Incubation of glycated human serum albumin (HSA) in 0.1 N NaOH led to the formation of CML whereas glycated HSA reduced by NaCNBH3 or non-glycated HSA did not generate CML. Nalpha-t-butyloxycarbonyl-Nepsilon-fructoselysine (Boc-FL), a model compound of Amadori product, was converted to CML under alkaline conditions. CML level of human sera (n=224) preincubated with 0.1 N NaOH correlated well with glycated albumin value (r=0.912) and hemoglobin A1c (r=0.797).
authors.affiliation: Department of Biochemistry, Kumamoto University School of Medicine, Honjo, Japan.
authors.forename: R
authors.initials: R
authors.lastname: Nagai
authors.forename: K
authors.initials: K
authors.lastname: Ikeda
authors.forename: Y
authors.initials: Y
authors.lastname: Kawasaki
authors.forename: H
authors.initials: H
authors.lastname: Sano
authors.forename: M
authors.initials: M
authors.lastname: Yoshida
authors.forename: T
authors.initials: T
authors.lastname: Araki
authors.forename: S
authors.initials: S
authors.lastname: Ueda
authors.forename: S
authors.initials: S
authors.lastname: Horiuchi
mesh_terms: D000596:Amino Acids / Q000032:analysis; D000911:Antibodies, Monoclonal / Q000276:immunology; D019270:Fructosamine / Q000031:analogs & derivatives* / Q000378:metabolism; D006442:Glycated Hemoglobin / Q000276:immunology; D017127:Glycation End Products, Advanced / Q000276:immunology / Q000378:metabolism*; D006801:Humans; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000276:immunology / Q000378:metabolism; D015416:Maillard Reaction; D012709:Serum Albumin / Q000378:metabolism; D012710:Serum Albumin, Bovine / Q000276:immunology; D012972:Sodium Hydroxide
chemical_list: D000596:Amino Acids; D000911:Antibodies, Monoclonal; D019270:Fructosamine; D006442:Glycated Hemoglobin; D017127:Glycation End Products, Advanced; D008239:Lysine; D012709:Serum Albumin; D012710:Serum Albumin, Bovine; D012972:Sodium Hydroxide; C048496:N(6)-carboxymethyllysine