Biomimetic Tweezers for N‐Glycans: Selective Recognition of the Core GlcNAc2 Disaccharide of the Sialylglycopeptide SGP

Author:

Milanesi Francesco12ORCID,Unione Luca34ORCID,Ardá Ana34ORCID,Nativi Cristina1ORCID,Jiménez‐Barbero Jesús3456ORCID,Roelens Stefano1ORCID,Francesconi Oscar1ORCID

Affiliation:

1. Department of Chemistry “Ugo Schiff” DICUS and INSTM University of Florence Polo Scientifico e Tecnologico I–50019 Sesto Fiorentino Firenze Italy

2. Magnetic Resonance Center CERM University of Florence Via L. Sacconi 6 I-50019 Sesto Fiorentino Firenze Italy

3. CICbioGUNE Basque Research & Technology Alliance (BRTA) Bizkaia Technology Park, Building 800 48160 Derio, Bizkaia Spain

4. Ikerbasque, Basque Foundation for Science Maria Diaz de Haro 3 48013 Bilbao Bizkaia Spain

5. Department of Organic Chemistry II Faculty of Science and Technology University of the Basque Country EHU-UPV 48940 Leioa Spain

6. Centro de Investigación Biomédica En Red de Enfermedades Respiratorias Madrid Spain

Abstract

AbstractIn recent years, glycomics have shown how pervasive the role of carbohydrates in biological systems is and how chemical tools are essential to investigate glycan function and modulate carbohydrate‐mediated processes. Biomimetic receptors for carbohydrates can carry out this task but, although significant affinities and selectivities toward simple saccharides have been achieved, targeting complex glycoconjugates remains a goal yet unattained. In this work we report the unprecedented recognition of a complex biantennary sialylglycopeptide (SGP) by a tweezers‐shaped biomimetic receptor, which selectively binds to the core GlcNAc2 disaccharide of the N‐glycan with an affinity of 170 μM. Because of the simple structure and the remarkable binding ability, this biomimetic receptor can represent a versatile tool for glycoscience, opening the way to useful applications.

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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