Synthesis of Casein-Related Peptides and Phosphopeptides. VIII. The Synthesis of Ser(P)-Containing Peptides by the Use of Z-Ser(PO3R2)-OH Derivatives
Australian Journal of Chemistry
44(2) 253 - 263
Published: 1991
Abstract
.The synthesis of five Z-Ser(PO3R2)-OH (R = phenyl, ethyl, methyl, benzyl, t-butyl) derivatives is described by a simple three-step synthetic procedure which features the use of either (A) diphenyl or dialkyl phosphorochloridate /pyridine or (B) dialkyl N,N-diethylphosphoramidite/1H-tetrazole-m-chloroperoxybenzoic acid for the phosphorylation of the serine hydroxy group. The benzyl phosphate derivative, Z-Ser(PO3Bzl2)-OH, was used in the benzyloxycarbonyl mode of peptide synthesis for the preparation of Z-Ser(PO3Bzl2)-Leu-OBzl and Z-Ser(PO3Bzl2)-Ser(PO3Bzl2)- OBzl which were deprotected by palladium- catalysed hydrogenolysis to give Ser(P)-Leu and Ser(P)-Ser(P) in high yields and high purity.
https://doi.org/10.1071/CH9910253
© CSIRO 1991