engleski

Peptide based artificial receptors for carbohydrate recognition.

Protein-mediated natural chiral carbohydrate recognition is one of the most sophisticated recognition processes in biological systems. This process mediates many important aspects of cell-cell recognition, such as bacterial adhesion to human tissue, inflammation, cell differentiation, tumor cell colonization and metastasis. However, due to its complexity and weak binding affinities, carbohydrate recognition by natural systems is still poorly understood. Studies on synthetic carbohydrate receptors could make significant contributions to a better understanding of this process and lead to the development of new analytical agents or therapeutics. Peptide based macrocyclic structures such as bicyclic peptide, are particularly interesting for the design of artificial carbohydrate receptor molecules because of their facile assembly using standard SPPS, and the three dimensional structure that would permit carbohydrate substrates to be encapsulated to afford polyvalent binding, enhancing therefore receptor’s selectivity and affinity. In addition, incorporated bipyridine aromatic units exhibit strong absorption and fluorescence emission bands, and complexation induced spectral changes can be exploited for the discrimination among variety of monosaccharide structures. To demonstrate suitability of bicyclic peptide structures for design of artificial carbohydrate receptors we have successfully prepared bicyclic peptide modeled on the cyclic cationic decapeptide antibiotic polymyxin B, which is known to bind the lipid A moiety of bacterial lipopolysaccharides with the high affinity. Combinatorial chemistry approach is applied to improve receptors binding properties and selectivity.

receptors, carbohydrate recognition, peptides

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