Glycopeptides by Linch-Pin C-H Activations for Peptide-Carbohydrate Conjugation by Manganese(I)-Catalysis

Chemistry. 2019 Aug 9;25(45):10585-10589. doi: 10.1002/chem.201902788. Epub 2019 Jul 15.

Abstract

Late-stage C-H glycosylations of structurally complex amino acids and peptides were accomplished by means of racemization-free manganese(I)-catalyzed C-H activation. Thus, glycosylative modifications proved to be viable by a linch-pin approach, featuring chemo- and site-selective C-H transformations. The peptide-saccharide conjugation provided modular access to structurally complex glycopeptides, likewise enabling the assembly of fluorescent-labelled glycopeptides.

Keywords: C−H activation; glycoconjugation; glycopeptides; manganese; natural products.

MeSH terms

  • Carbohydrates / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Glycopeptides / chemical synthesis
  • Glycopeptides / chemistry*
  • Glycosylation
  • Hydrogen / chemistry
  • Manganese / chemistry*
  • Peptides / chemistry*

Substances

  • Carbohydrates
  • Glycopeptides
  • Peptides
  • Manganese
  • Carbon
  • Hydrogen