N?O-Acyl shift in Fmoc-based syntheses of phosphopeptides.

H. Eberhard, O. Seitz – 2008

Synthetic phosphopeptides are frequently used as chemical probes to explore protein–protein interactions involved in cellular signal transduction. Most commonly, the solid-phase synthesis of phosphotyrosine-containing peptides is performed by applying the Fmoc-strategy and N-Fmoc-protected tyrosine derivatives bearing acid-labile phospho protecting groups. We observed a side-reaction, the isomerisation at threonine, which furnishes depsipeptides. It is shown that the rate of N→O-acyl migration depends on the sequence context. Depsipeptides were formed most rapidly when the phosphotyrosine was located in the +2 position. Furthermore, different phosphotyrosine building blocks were compared and a suitable method that provides phosphopeptides in enhanced purity and yield is suggested.

Titel
N?O-Acyl shift in Fmoc-based syntheses of phosphopeptides.
Verfasser
H. Eberhard, O. Seitz
Datum
2008
Kennung
10.1039/b718568e
Zitierweise
Org. Biomol. Chem. 2008, 6, 1349-1355.
Art
Text
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