TOMBU and COMBU as Novel Uronium-type peptide coupling reagents derived from Oxyma-B

Molecules. 2014 Nov 18;19(11):18953-65. doi: 10.3390/molecules191118953.

Abstract

Here we describe two novel uronium salts, TOMBU and COMBU, derived from the recently described Oxyma-B for use in peptide bond synthesis. These coupling reagents are more stable than COMU in DMF. Furthermore, using various peptide synthetic models in solution and solid-phase synthesis, we reveal that they show better performance than HBTU in terms of preserving chiral integrity and coupling yields, but slightly worse performance than COMU.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Barbiturates / chemistry*
  • Indicators and Reagents / chemistry*
  • Oximes / chemistry*
  • Peptides / chemistry*
  • Solid-Phase Synthesis Techniques / methods
  • Solutions / chemistry
  • Triazoles / chemistry

Substances

  • 5-(hydroxyimino)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione
  • Barbiturates
  • Indicators and Reagents
  • Oximes
  • Peptides
  • Solutions
  • Triazoles