https://doi.org/10.15255/KUI.2006.030
Published: Kem. Ind. 56 (3) (2007) 115–122
Paper reference number: KUI-30/2006
Paper type: Conference paper
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Synthetic Glycoconjugates: Models for Studying Interactions in Biomolecular Recognition and Sugar-Induced Modifications of Peptides/Proteins

Š. Horvat

Abstract

Although the biological and medical importance of complex carbohydrates and glycoconjugates is firmly established, many of the molecular details of how these intriguing compounds accomplish their functions are not understood well. Unraveling these molecular mechanisms is very important since our understanding of the role of glycoconjugates in nature has traditionally fallen far behind the accumulated knowledge on other biopolymers such as proteins and nucleic acids. The synthesis of pure, well-defined glycoconjugates of bioactive peptides is essential to the study of the biological processes that they mediate. This paper covers the methods for glycoconjugate assembly and biological activity screening. Within this context, the impact of the carbohydrate moiety on receptor selectivity, chemical and metabolic stability will be addressed. The diversity and complexity of nonenzymatic glycation products found in naturally occurring peptides/proteins hasten the need to clarify the sequence of reactions that carbohydrate adducts undergo and to find biomarkers of specific sugar-peptide structures. Addressing these issues, it is demonstrated how the structure of the sugar moiety controls the formation of glycation products from the endogenous opioid peptide, Leu-enkephalin. It is shown that the information gained from carbohydrate-peptide model systems provides a novel mechanism for the generation of the glycation (Maillard) reaction intermediates under physiological conditions and better insights into the damage to endogenous peptides as a result of glycation by reducing sugars in vivo.

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Keywords

bioactivity, enkephalin, glycation, glycoconjugates, opioid peptides, synthesis