PyAOP

CAS 156311-83-0, Cat. No EN300-7492597

Activator in peptide coupling, triphosphorylating reagent for C, N, and O Nucleophiles

PyAOP was originally a reagent activator for carboxylic acids but recently found its uses in functionalizing intact trimetaphosphate. It is in the form of colorless crystals, soluble in CH₂Cl₂, CHCl₃, DMF, DMSO, NMP, THF, CH₃CN, and acetone. As a reagent-activator for carboxylic acids in peptide coupling reactions, it doesn’t react with primary amines, in contrast to the corresponding uronium/aminium salts which lead to guanidino derivatives. Also, it is among the most reactive coupling reagents, but at the price of stability, which makes it less effective in automated solid-phase peptide synthesis. The functionalization of trimetaphosphate can be done with primary alcohols, amines, secondary amines, and Wittig reagents to form phosphorus ylide in moderate yield. This reagent can be applied to the triphosphorylation of nucleosides.

Synonyms: (7-Azabenzotriazol-1-yloxy)tris (pyrrolidino)phosphonium Hexafluorophosphate; tri-Pyrrolidinyl[3H-1,2,3-triazolo (4,5-b)pyridin-3-yloxy]phosphonium hexafluorophosphate