Conversion of Amadori product of Maillard reaction to Nepsilon-(carboxymethyl)lysine in alkaline condition.
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).
Nagai
R
R
Department of Biochemistry, Kumamoto University School of Medicine, Honjo, Japan.
Ikeda
K
K
Kawasaki
Y
Y
Sano
H
H
Yoshida
M
M
Araki
T
T
Ueda
S
S
Horiuchi
S
S
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
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