Immobilized coupling reagents: synthesis of amides/peptides

ACS Comb Sci. 2014 Nov 10;16(11):579-601. doi: 10.1021/co500126y. Epub 2014 Oct 24.

Abstract

The primary idea of using immobilized reagents in organic synthetic chemistry is to simplify the downstream process, product workup and isolation, and therefore avoiding time-consuming and expensive chromatographic separations, which are intrinsic to every synthetic process. Numerous polymer-bounded reagents are commercially available and applicable to almost all kinds of synthetic chemistry conversions. Herein, we have covered all known supported-coupling reagents and bases which have had a great impact in amide/peptide bond formation. These coupling reagents have been used for the activation of a carboxyl moiety; thus generating an active acylating species that is ready to couple with an amine nucleophile liberating the amide/peptide and polymeric support which can be regenerated for reuse. This also addresses a large variety of anchored coupling reagents, additives, and bases that have only been employed in amide/peptide syntheses during the last six decades.

Keywords: combinatorial chemistry; coupling additive; high-throughput organic synthesis; solid-phase synthesis; stand-alone coupling reagent.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Combinatorial Chemistry Techniques / methods
  • Indicators and Reagents / chemistry
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Polymers / chemistry
  • Solid-Phase Synthesis Techniques / methods*

Substances

  • Amides
  • Indicators and Reagents
  • Peptides
  • Polymers