J. Perich, D. L. Nguyen, E. Reynolds
Aug 5, 1991
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron Letters
Abstract
The O-phosphotyrosyl-containing peptide, Ala-Glu-Tyr(P)-Ser-Ala, was prepared by a methodology which featured ‘phosphite-triester’ phosphorylation of a resin-bound Tyr-containing peptide. The peptide-resin was assembled by Fmoc/solid phase peptide synthesis using HBTU as the coupling reagent and the tyrosyl residue incorporated as Fmoc-Tyr-OH. The peptide-resin was phosphorylated using di-t-butylN,N-diethylphosphonamidite/ 1H-tetrazole followed by m-chloroperoxybenzoic acid oxidation. Simultaneous peptide-resin cleavage and peptide deprotection was effected by 5% anisole/TFA to give the crude Tyr(P)-peptide in high yield and in >95% purity.