title: Multivalent presentation of carbohydrates by 3(14)-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition.
abstract: 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.
authors.affiliation: Department of Chemistry, Garware Research Centre, Savitribai Phule Pune University (Formerly University of Pune), Pune - 411 007, India. ddd@chem.unipune.ac.in.
authors.forename: Nitin J
authors.initials: NJ
authors.lastname: Pawar
authors.forename: Ulf
authors.initials: U
authors.lastname: Diederichsen
authors.forename: Dilip D
authors.initials: DD
authors.lastname: Dhavale
mesh_terms: D003208:Concanavalin A / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D007785:Lactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D017433:Protein Structure, Secondary
chemical_list: D006020:Glycopeptides; D003208:Concanavalin A; D005947:Glucose; D007785:Lactose; D008358:Mannose; D005690:Galactose