Multivalent thioglycopeptoids via photoclick chemistry: potent affinities towards LecA and BC2L-A lectins

Chem Commun (Camb). 2015 Aug 7;51(61):12301-4. doi: 10.1039/c5cc04646g.

Abstract

Solution-phase synthesis of linear and cyclic β- and α,β-peptoids was coupled to photo-induced thiol-ene coupling reaction to readily access multivalent thioglycoclusters. A tetrameric cyclic β-peptoid scaffold displaying 1-thio-β-d-galactose or 1-thio-α-d-mannose has revealed by ITC experiments efficient binding potency for bacterial lectins LecA and BC2L-A, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Burkholderia cenocepacia / chemistry*
  • Click Chemistry*
  • Lectins / chemistry*
  • Molecular Structure
  • Peptoids / chemical synthesis*
  • Peptoids / chemistry
  • Photochemical Processes
  • Pseudomonas aeruginosa / chemistry*
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry

Substances

  • Lectins
  • Peptoids
  • Sulfhydryl Compounds