Ester-linked glycopeptides as tools for studies of biological phenomena

Horvat, Štefica; Jerić, Ivanka; Varga-Defterdarović, Lidija; Roščić, Maja; Horvat, Jaroslav (2001) Ester-linked glycopeptides as tools for studies of biological phenomena. Croatica Chemica Acta, 74 (4). pp. 787-799. ISSN 0011-1643

PDF - Published Version
Download (124kB)

Official URL: http://public.carnet.hr/ccacaa/co014.html

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.

Item Type:

Article

Uncontrolled Keywords:

glycopeptides; enkephalin; opioid; imidazolidinone; Maillard; glycation; glycation end-products; maillard reaction; amino-acids; intramolecular rearrangement; cell activation; imidazolidinones; identification; chemistry; proteins; receptor

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects: