Rapid access to Asp/Glu sidechain hydrazides as thioester precursors for peptide cyclization and glycosylation

Chem Commun (Camb). 2021 Feb 1;57(8):1006-1009. doi: 10.1039/d0cc07404g.

Abstract

Head-to-sidechain macrocylic peptides, and neoglycopeptides, were readily prepared by site-specific amidation of aspartic and glutamic acid sidechain hydrazides. Hydrazides, serving as latent thioesters, were introduced through regioselective opening of the corresponding Nα-Fmoc protected anhydride precursors.

MeSH terms

  • Aspartic Acid / chemistry*
  • Cyclization
  • Glutamic Acid / chemistry*
  • Glycosylation
  • Macrocyclic Compounds
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Protein Conformation

Substances

  • Macrocyclic Compounds
  • Peptides, Cyclic
  • Aspartic Acid
  • Glutamic Acid