Amide and Peptide Bond Formation in Water at Room Temperature

Org Lett. 2015 Aug 21;17(16):3968-71. doi: 10.1021/acs.orglett.5b01812. Epub 2015 Aug 7.

Abstract

A general and environmentally responsible method for the formation of amide/peptide bonds in an aqueous micellar medium is described. Use of uronium salt (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate (COMU) as a coupling reagent, 2,6-lutidine, and TPGS-750-M represents mild conditions associated with these valuable types of couplings. The aqueous reaction medium is recyclable leading to low E Factors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Imines / chemistry
  • Indicators and Reagents
  • Molecular Structure
  • Morpholines / chemistry
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Pyridines / chemistry
  • Surface-Active Agents / chemistry
  • Temperature
  • Water / chemistry*

Substances

  • 1-((1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylaminomorpholinomethylene))methanaminium
  • Amides
  • Imines
  • Indicators and Reagents
  • Morpholines
  • Peptides
  • Pyridines
  • Surface-Active Agents
  • Water
  • 2,6-lutidine