A fascinating journey into history: exploration of the world of isonitriles en route to complex amides

Angew Chem Int Ed Engl. 2012 Mar 19;51(12):2834-48. doi: 10.1002/anie.201106628. Epub 2012 Feb 24.

Abstract

We describe herein our recent explorations in the field of isonitrile chemistry. An array of broadly useful coupling methodologies has been developed for the formation of peptidyl and glycopeptidyl amide bonds. We further describe the application of these methods to the syntheses of complex systems, including the cyclic peptide cyclosporine A, constrained peptide systems, and heterocycles.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Amides / chemistry*
  • Carboxylic Acids / chemistry
  • Cyclosporine / chemical synthesis
  • Cyclosporine / chemistry
  • Glycopeptides / chemical synthesis
  • Glycopeptides / chemistry
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry
  • Nitriles / chemistry*
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry

Substances

  • Amides
  • Carboxylic Acids
  • Glycopeptides
  • Heterocyclic Compounds
  • Nitriles
  • Peptides
  • Sulfhydryl Compounds
  • Cyclosporine