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Bicyclic Peptide Based Lectinomimic

Rodriguez, Maria C.; Bionda, Nina; Johnson, Claudia A.; Jakas, Andreja; Čudić, Predrag (2017) Bicyclic Peptide Based Lectinomimic. Croatica chemica acta, 90 (4). pp. 699-705. ISSN 0011-1643

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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.

Item Type: Article
Uncontrolled Keywords: Aqueous media ; artificial receptors ; bicyclic peptides ; lectinomimics ; monosaccharide binding
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Artificial Receptors for Bacillus Anthracis Sepecific Anthrose DetectionJakas, AndrejaSfP 983154UNSPECIFIED
Depositing User: Andreja Jakas
Date Deposited: 18 Jul 2018 12:58
DOI: 10.5562/cca3295

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