
%0 Journal Article
%A Perich, JW 
%A Johns, RB 
%T Synthesis of Casein-Related Peptides and Phosphopeptides. III. The Unexpected Dephosphorylative Rearrangement of the Simple Model Phosphopeptides Ac-Ser(PO<sub>3</sub>Bzl<sub>2</sub>)-NHMe and Ac-Ser(Po<sub>3</sub>H<sub>2</sub>)-NHMe
%J Australian Journal of Chemistry
%D 1990/10/01
%V 43
%N 10
%P 1603-1608
%K 
%R https://doi.org/10.1071/CH9901603
%U https://www.publish.csiro.au/paper/CH9901603 
%X The simple phosphopeptide, Ac-Ser(PO3Bzl2)-NHMe , was found to be subject to a dephosphorylative rearrangement and gave H-Ser-NHMe .( BzlO )2PO2H after 12 months at 20&#176;C. This dephosphorylative rearrangement process is proposed to proceed by an O to N phosphorus shift followed by acid hydrolysis of the N-acetyl group. Alternatively, the simple phospho-peptide, Ac-Ser(PO3H2)-NHMe, was found to undergo conversion into H-Ser- NHMe.H3PO4 over a period of four years, this process being established by a 13C n.m.r. spectroscopy study to proceed through initial acid hydrolysis of the N-acetyl group followed by phosphate loss. 
