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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. III. The Unexpected Dephosphorylative Rearrangement of the Simple Model Phosphopeptides Ac-Ser(PO3Bzl2)-NHMe and Ac-Ser(Po3H2)-NHMe

JW Perich and RB Johns

Australian Journal of Chemistry 43(10) 1603 - 1608
Published: 1990

Abstract

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°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.

https://doi.org/10.1071/CH9901603

© CSIRO 1990

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