Preparation of Nα-Boc 4-O-Diethylphospho-L-azatyrosine, a Regent Potentially Useful for the Synthesis of Signal Transduction Related Peptides
31 December 2000 (online)
Preparation of the phosphorylated azatyrosine analogue, 2(S)-Nα-Boc-3-[5’-(diethyl phosphoryloxy)-2’-pyridyl]propionate (3), is reported. This compound is designed for the solid-phase synthesis of cell signal transduction peptides containing a phosphotyrosyl reside bearing a nitrogen atom in the tyrosyl aromatic ring. An important aspect of the synthetic approach is the use of diethyl phosphate functionality for phenolic hydroxyl protection during palladium-mediated coupling.
azatyrosine - phosphotyrosine - signal transduction - SH2 domain