Synthesis and lectin binding ability of glycosamino acid-calixarenes exposing GlcNAc clusters

Grazia M L Consoli; Francesca Cunsolo; Corrada Geraci; Valentina Sgarlata

doi:10.1021/ol0485767

Synthesis and lectin binding ability of glycosamino acid-calixarenes exposing GlcNAc clusters

Org Lett. 2004 Nov 11;6(23):4163-6. doi: 10.1021/ol0485767.

Authors

Grazia M L Consoli¹, Francesca Cunsolo, Corrada Geraci, Valentina Sgarlata

Affiliation

¹ Istituto di Chimica Biomolecolare, Sezione di Catania CNR, Via del Santuario 110, I-95028 Valverde (CT), Italy.

PMID: 15524433
DOI: 10.1021/ol0485767

Abstract

Novel calix[4 or 8]arene-based glycoconjugates exposing terminal N-acetyl-D-glucosamine clusters have been synthesized using amino acid-calixarenes as building blocks. The obtained glycosamino acid-calixarenes 9b-14b have lectin-binding ability and amplified inhibitory effects on erythrocyte agglutination induced by wheat germ (Triticum vulgaris) agglutinin (WGA). The inhibitory ability is dependent on the presence of the spacer and on the shape and rigidity of the calixarene skeleton.

MeSH terms

Acetylglucosamine / chemistry*
Calixarenes / chemical synthesis*
Calixarenes / chemistry
Lectins / metabolism*
Molecular Structure
Protein Binding

Substances

Lectins
Calixarenes
Acetylglucosamine