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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Casein-Related Peptides and Phosphopeptides. VIII. The Synthesis of Ser(P)-Containing Peptides by the Use of Z-Ser(PO3R2)-OH Derivatives

JW Perich, PF Alewood and RB Johns

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

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