Chemoselective synthesis of peptides containing major advanced glycation end-products of lysine and arginine

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Abstract

Useful methodologies have been developed, enabling the straightforward synthesis of peptides containing Nε-(carboxymethyl)-L-lysine (CML) and Nε-(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. Copyright Blackwell Munksgaard, 2005.

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Gruber, P., & Hofmann, T. (2005). Chemoselective synthesis of peptides containing major advanced glycation end-products of lysine and arginine. Journal of Peptide Research, 66(3), 111–124. https://doi.org/10.1111/j.1399-3011.2005.00279.x

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