Multivalent presentation of carbohydrates by 3(14)-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition

• Published in: Organic & biomolecular chemistry Vol. 13; no. 46; p. 11278
• Main Authors: Pawar, Nitin J, Diederichsen, Ulf, Dhavale, Dilip D
• Format: Journal Article
• Language: English
• Published: England 14-12-2015
• Subjects: Concanavalin A - chemistry; Galactose - analogs & derivatives; Galactose - chemical synthesis; Glucose - analogs & derivatives; Glucose - chemical synthesis; Glycopeptides - chemical synthesis; Glycopeptides - chemistry; Lactose - analogs & derivatives; Lactose - chemical synthesis; Mannose - analogs & derivatives; Mannose - chemical synthesis; Protein Structure, Secondary
• ISSN: 1477-0539
• DOI: 10.1039/c5ob01673h

A well defined 314-helical tetravalent β-galactopeptide site-specific functionalised template (SSFT) 1 was prepared containing d-galactose units, with free anomeric carbons as the aldehyde tags, and was explored via ligation with different aminoxy sugars (α-/β-d-glucose, α/β-d-galactose, α-d-mannose and β-d-lactose) to get 314-helical carbohydrate-functionalised multivalent glycoconjugates 2-7. Preliminary recognition studies of tetramannosyl glycoconjugate 4 with a specific lectin (concanavalin A) using fluorescence anisotropy showed an increase in binding affinity and the multivalency effect was found to be increased by 6.5 times per glycan.