Functionalized High Mannose-Specific Lectins for the Discovery of Type I Mannosidase Inhibitors

Angew Chem Int Ed Engl. 2021 May 25;60(22):12313-12318. doi: 10.1002/anie.202101249. Epub 2021 Apr 26.

Abstract

An engineered cyanovirin-N homologue that exhibits specificity for high mannose N-glycans has been constructed to aid type I α 1,2-mannosidase inhibitor discovery and development. Engineering the lectins C-terminus permitted facile functionalization with fluorophores via a sortase and click strategy. The resulting lectin constructs exhibit specificity for cells presenting high mannose N-glycans. Importantly, these lectin constructs can also be applied to specifically assess changes in cell surface glycosylation induced by type I mannosidase inhibitors. Testing the utility of these lectin constructs led to the discovery of type I mannosidase inhibitors with nanomolar potency. Cumulatively, these findings reveal the specificity and utility of the functionalized cyanovirin-N homologue constructs, and highlight their potential in analytical contexts that require high mannose-specific lectins.

Keywords: bioconjugation; lectin; mannosidase inhibitors; natural products; protein modifications.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / metabolism
  • Amino Acid Motifs
  • Aminoacyltransferases / chemistry
  • Bacterial Proteins / chemistry
  • Cell Line
  • Cysteine Endopeptidases / chemistry
  • Drug Design
  • Fluorescent Dyes / chemistry
  • Glycosylation
  • Humans
  • Lectins / chemistry*
  • Lectins / metabolism
  • Mannose / chemistry
  • Mannose / metabolism
  • Mannosidases / antagonists & inhibitors*
  • Mannosidases / metabolism
  • Microscopy, Fluorescence

Substances

  • Alkaloids
  • Bacterial Proteins
  • Fluorescent Dyes
  • Lectins
  • kifunensine
  • cyanovirin N
  • Aminoacyltransferases
  • sortase A
  • Mannosidases
  • mannosyl-oligosaccharide 1,2-alpha-mannosidase
  • Cysteine Endopeptidases
  • Mannose