Multivalent presentation of carbohydrates by 314-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognitionElectronic supplementary information (ESI) available: Copies of 1H and 13C NMR spectrum for the new compound and HPLC traces of purified glycoconjugates 1-7. See DOI: 10.1039/c5ob01673h

• Main Authors: Pawar, Nitin J, Diederichsen, Ulf, Dhavale, Dilip. D
• Format: Journal Article
• Language: English
• Published: 17.11.2015
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c5ob01673h

A well defined 3 14 -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 3 14 -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. A tetrameric glycoconjugate template, SSFT 1 , was coupled with a variety of six aminooxy sugars to achieve multivalent glycoconjugates 2-7 .