title: Chemoselective synthesis of peptides containing major advanced glycation end-products of lysine and arginine.
abstract: Useful methodologies have been developed, enabling the straightforward synthesis of peptides containing N(epsilon)-(carboxymethyl)-L-lysine (CML) and N(epsilon)-(carboxyethyl)-L-lysine (CEL), the major glycation end-products of lysine. These lysine derivatives were successfully incorporated into growing peptide chains via standard Fmoc/Ot-Bu peptide synthesis procedures. For the synthesis of peptides containing major glycation end-products of arginine, synthetic routes have been developed enabling the transformation of ornithine residues in peptides into the well-known arginine-derived advanced glycation end-products (AGEs) Glarg, carboxymethyl-L-arginine (CMA), MG-H1, MG-H2, MG-H3, and carboxyethyl-L-arginine (CEA), respectively, by means of special modifying agents. Furthermore, it was shown that Glarg-containing peptides become quantitatively hydrolyzed into CMA-peptides under physiologic conditions. A similar reaction was observed in case of a MG-H3-peptide, which turned into a CEA-peptide under these conditions.
authors.affiliation: Deutsche Forschungsanstalt für Lebensmittelchemie, Lichtenbergstr. 4, D-85748 Garching, Germany.
authors.forename: P
authors.initials: P
authors.lastname: Gruber
authors.forename: T
authors.initials: T
authors.lastname: Hofmann
mesh_terms: D000595:Amino Acid Sequence; D001120:Arginine / Q000737:chemistry*; D002853:Chromatography, Liquid; D017127:Glycation End Products, Advanced / Q000737:chemistry*; D008239:Lysine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D020539:Sequence Analysis, Protein
chemical_list: D017127:Glycation End Products, Advanced; D010455:Peptides; D001120:Arginine; D008239:Lysine