title: Lysine proximity significantly affects glycation of lysine-containing collagen model peptides.
abstract: Advanced glycation end products (AGE) are known to cause diabetes complications in hyperglycemia patients. In this study we prepared hetero-trimers of collagen model peptides comprising Ac-(Pro-Hyp-Gly)(5)-Pro-Lys-Gly-(Pro-Hyp-Gly)(5)-Ala-NH(2) (4) and Ac-(Pro-Hyp-Gly)(11)-Ala-NH(2) (5) to investigate the clustering effect of lysine on AGE formation. The formation rate of carboxymethyllysine over several months was determined for the mixtures of peptides 4 and 5 at (3:0), (2:1) and (1:2) in the presence of glucose. The contents of carboxymethyllysine were significantly enhanced for (3:0) and (2:1) as compared with (1:2), suggesting that the proximity of lysine residues in the trimers accelerated formation of the AGE. Furthermore, a lysine dimerization moiety (GOLD) was identified for the first time from AGEs of glucose origin, which implied the significance of GOLD in oligomerization of collagens and other long-life proteins.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Asuka
authors.initials: A
authors.lastname: Kitamura
authors.forename: Kouta
authors.initials: K
authors.lastname: Matsui
authors.forename: Keiichi
authors.initials: K
authors.lastname: Konoki
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Matsumori
authors.forename: Michio
authors.initials: M
authors.lastname: Murata
authors.forename: Toru
authors.initials: T
authors.lastname: Kawakami
authors.forename: Saburo
authors.initials: S
authors.lastname: Aimoto
mesh_terms: D003094:Collagen / Q000737:chemistry* / Q000378:metabolism; D017127:Glycation End Products, Advanced / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D006801:Humans; D008239:Lysine / Q000737:chemistry* / Q000378:metabolism; D013058:Mass Spectrometry; D010446:Peptide Fragments / Q000737:chemistry* / Q000378:metabolism; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D017127:Glycation End Products, Advanced; D010446:Peptide Fragments; D010455:Peptides; D003094:Collagen; D008239:Lysine