Intact glycation end products containing carboxymethyl-lysine and glyoxal lysine dimer obtained from synthetic collagen model peptide.
Advanced glycation end products (AGE) are accumulated in human tissues when long-lived proteins are glycated due to hyperglycemia and/or aging. In this study, we synthesized a collagen model peptide, Ac-(Pro-Hyp-Gly)(5)-Pro-Lys-Gly-(Pro-Hyp-Gly)(5)-Ala-NH(2) to investigate intact AGEs in peptides. The peptide formed a stable triple helix structure, and was subjected to glycation reactions with glucose, ribose and glyoxal. Besides carboxymethyl-lysine in the peptide, a conjugated form linked with glyoxal lysine dimer (GOLD) was detected upon treatment with glyoxal. This is the first example of intact glycation-derived dimers of peptides retaining intrinsic protein structures.
Yamada
Hiroaki
H
Department of Chemistry, Graduate School of Science, Osaka University, 1-16 Machinakeyama, Toyonaka, Osaka 560-0043, Japan.
Sasaki
Tomoko
T
Niwa
Sachiko
S
Oishi
Tohru
T
Murata
Michio
M
Kawakami
Toru
T
Aimoto
Saburo
S
D000595:Amino Acid Sequence; D024042:Collagen Type I / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D017127:Glycation End Products, Advanced / Q000737:chemistry*; D006037:Glyoxal / Q000737:chemistry*; D006801:Humans; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry; D017434:Protein Structure, Tertiary
D024042:Collagen Type I; D017127:Glycation End Products, Advanced; D010446:Peptide Fragments; D006037:Glyoxal; C048496:N(6)-carboxymethyllysine; D008239:Lysine