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.
Yahya E Jad  1 ,  Sherine N Khattab  2 ,  Beatriz G de la Torre  3 ,  Thavendran Govender  4 ,  Hendrik G Kruger  5 ,  Ayman El-Faham  2 ,  Fernando Albericio  6
Affiliations
  • 1. Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa. [email protected].
  • 2. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt. [email protected].
  • 3. Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa. [email protected].
  • 4. Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa. [email protected].
  • 5. Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa. [email protected].
  • 6. Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa. [email protected].
PMID: 25412042 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.

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