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Review article

Ester-linked Glycopeptides as Tools for Studies of Biological Phenomena

Štefica Horvat ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Ivanka Jerić ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Lidija Varga-Defterdarović ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Maja Roščić ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Jaroslav Horvat ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia


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Abstract

Modifications of plasma proteins, structural proteins and other macromolecules by glycation (the Maillard reaction) contribute to the development of accelerated atherosclerosis and other complications in diabetes and are also involved in the pathogenesis of aging. Monosaccharide esters, which mimic the reactivity of sugar 6-phosphate esters in nonenzymatic glycations, were prepared from endogenous opioid peptide leucine-enkephalin (Tyr-Gly-Gly-Phe-Leu), smaller peptides of different lengths (Tyr-Pro-Phe-Val, Tyr-Pro-Phe, Tyr-Pro) and from only one amino acid (Tyr) and were used as model compounds for a Study of the Maillard reaction in vitro. It was found that these compounds readily undergo intramolecular reactions leading to different types of products, such as Amadori compounds, imidazolidinones, glycosylamine, diketopiperazine, pyrrololactone, etc. The obtained results demonstrate that the Chemical properties of the glycopeptides studied are determined by the structure and length of the peptide chain, suggesting that similar products may be also generated in the early stages of the Maillard reaction in vivo.

Keywords

glycopeptides, enkephalin, opioid, imidazolidinone, Maillard, glycation

Hrčak ID:

131955

URI

https://hrcak.srce.hr/131955

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