Jump to main content
Jump to site search

Issue 16, 2010
Previous Article Next Article

PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts

Author affiliations

Abstract

Recent studies described the great impact of a non-benzotriazolic family of coupling reagents based on ethyl 2-cyano-2-(hydroxyimino)acetate, Oxyma, as a powerful coupling methodology for peptide synthesis. Here we present the synthesis and evaluation of the derived phosphonium salts O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and tetrafluoroborate (PyOxB). Both coupling reagents exhibited higher capacity to suppress racemization in various peptide models and enhanced solubility in DMF and DCM than benzotriazole-based reagents. In addition, the hexafluorophosphate analog PyOxP, combined excellent stability with outstanding efficiency in the assembly of demanding penta and decapeptides that include consecutive Aib residues. Cyclization models revealed the advantages of PyOxP, which rendered a higher percentage of cyclic material than other known potent phosphonium salts.

Graphical abstract: PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts

Back to tab navigation

Supplementary files

Article information


Submitted
12 Mar 2010
Accepted
19 May 2010
First published
17 Jun 2010

Org. Biomol. Chem., 2010,8, 3665-3673
Article type
Paper

PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts

R. Subirós-Funosas, A. El-Faham and F. Albericio, Org. Biomol. Chem., 2010, 8, 3665
DOI: 10.1039/C003719B

Social activity

Search articles by author

Spotlight

Advertisements