Naslov
Bicyclic Peptide Based Lectinomimic

Autori
Rodriguez, Maria C. ; Bionda, Nina ; Johnson, Claudia A. ; Jakas, Andreja ; Čudić, Predrag

Izvornik
Croatica chemica acta (0011-1643) 90 (2017), 4; 699-705

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Aqueous media ; artificial receptors ; bicyclic peptides ; lectinomimics ; monosaccharide binding

Sažetak
Peptide based lectin mimetics represent an attractive approach for the development of artificial carbohydrate receptors that might find application in bio-analytical and medicinal fields. Taking into consideration the structure of typical lectin binding site, we have designed a novel artificial receptor molecule possessing a rigid three-dimensional structure, hydrogen-bonding site and lipophilic binding pocket to promote hydrophobic interaction and hydrogen-bonding. A new solid- phase synthetic approach that allows complete synthesis of desired bicyclic peptide 1 on the solid support was developed. CD spectra of peptides 1 and 2 indicate that the structure of 1 is rather rigid and preorganised for the three-dimensional monosaccharide substrates binding. The binding affinities of bicyclic peptide receptor 1 toward various carbohydrate substrates at physiologically relevant conditions were estimated by UV/vis and fluorimetric titration experiments, and the observed values are in the millimolar range. With these results we have demonstrated that the bicyclic peptide 1 represent a promising basis for the design of new and more efficient carbohydrate receptors that may have broader application in bio-analytical or medicinal field.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA