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A New Reagent for Polypeptide Synthesis: μ‐Oxo‐bis‐[tris‐(dimethylamino)‐phosphonium]‐bis‐tetrafluoroborate
Author(s) -
Bates Arnold J.,
Galpin Ian J.,
Hallett Allan,
Hudson Derek,
Kenner George W.,
Ramage Robert,
Sheppard Robert C.
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580306
Subject(s) - chemistry , tetrafluoroborate , reagent , tris , phosphonium , oxazolone , toluene , medicinal chemistry , organic chemistry , condensation , polymer chemistry , ionic liquid , catalysis , biochemistry , physics , thermodynamics
The products 1 and 2 (X = OTs) have been isolated from the reaction between hexamethylphosphortriamide and p ‐toluene sulfonic anhydride and the latter converted into μ‐oxo‐bis‐[tris‐(dimethylamino)‐phosphonium]‐bis‐tetrafluoroborate 2 (X = BF 4 ). This is a practical reagent for the formation of the peptide link. Where racemisation is possible via oxazolone formation this can be decreased by the addition of 1‐hydroxybenzotriazole or N‐hydroxysuccinimide. These additives may also increase the efficiency of condensation at glycine and proline residues.