83871-06-1Relevant articles and documents
A convenient method for the one-step synthesis of phosphonic peptides
Skoreński, Marcin,Oleksyszyn, Józef,Sieńczyk, Marcin
supporting information, p. 4975 - 4977 (2013/09/02)
A novel and efficient method for the synthesis of peptidyl derivatives of 1-aminoalkylphosphonate diaryl esters is presented. Phosphonic peptides were obtained in one step via an amidoalkylation reaction using amides of N-protected amino acids or peptides, triphenyl phosphite, and an appropriate aldehyde.
PyOxP and PyOxB: The Oxyma-based novel family of phosphonium salts
Subiros-Funosas, Ramon,El-Faham, Ayman,Albericio, Fernando
experimental part, p. 3665 - 3673 (2010/09/06)
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.
Potential thyroliberin affinity labels. II: Chloroacetyl substituted phenylalanyl prolineamides
Goebel,Currie,Bowers
, p. 1062 - 1064 (2007/10/02)
Three analogs of thyroliberin (I) were prepared. These compounds, N-m-chloroacetylbenzoyl-phenylalanyl-prolineamide (VIa), N-p-chloroacetylbenzoyl-phenylalanyl-prolineamide (VIb) and N-chloroacetyl-alanyl-phenylalanyl-prolineamide (IX), were designed as potential I antagonist affinity labels. However, no significant antagonist activity was observed. Compounds VIa and IX were found to have weak agonist activity. Cyclo (Phe-Pro) an analog of the I metabolite, cyclo (His-Pro), was found, however, to have significant I antagonist activity, but no agonist activity.