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Molecules 2014, 19(11), 18953-18965; doi:10.3390/molecules191118953

TOMBU and COMBU as Novel Uronium-Type Peptide Coupling Reagents Derived from Oxyma-B

1
Catalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal, Durban 4001, South Africa
2
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
3
School of Chemistry, Yachay Tech, Yachay City of Knowledge, 100119-Urcuqui, Ecuador
4
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
5
School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
6
Institute for Research in Biomedicine (IRB Barcelona), Baldiri Reixac 10, Barcelona, 08028, Spain
7
CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Barcelona 08028, Spain
8
Department of Organic Chemistry, University of Barcelona, Barcelona, 08028, Spain
*
Authors to whom correspondence should be addressed.
Received: 19 October 2014 / Revised: 19 October 2014 / Accepted: 5 November 2014 / Published: 18 November 2014
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: coupling reagents; solid-phase peptide synthesis; peptide synthesis; Oxyma-B; amino acids coupling reagents; solid-phase peptide synthesis; peptide synthesis; Oxyma-B; amino acids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Jad, Y.E.; Khattab, S.N.; de la Torre, B.G.; Govender, T.; Kruger, H.G.; El-Faham, A.; Albericio, F. TOMBU and COMBU as Novel Uronium-Type Peptide Coupling Reagents Derived from Oxyma-B. Molecules 2014, 19, 18953-18965.

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