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DOI: 10.1055/s-1998-3131
Preparation of Phospho-l-Azatyrosine Suitably Protected for the Synthesis of Signal Transduction Related Peptides. A Correction
Publication History
Publication Date:
31 December 2000 (online)
Synthesis of Nα-Fmoc 4-O,O-(di-tert-butyl)phospho-L-azatyrosine (6) and its use in Fmoc-based solid-phase peptide synthesis are reported. The di-tert-butyl phospho protecting groups were removed during TFA-mediated cleavage of the finished peptide (10) from the resin, providing the free phosphoazatyrosine-containing peptide directly. This is in contrast to diethyl phospho protection we previously reported [Ye, B.; Otaka, A.; Burke, T. R., Jr. Synlett 1996, 459-460] in which the diethyl protection has proven impractical to remove. Due to incorrect assignment of starting material, the title compound of this latter report should be corrected to the isomeric L-β-(3-hydroxy-2-pyridyl)-alanine compound (5).
azatyrosine - phosphotyrosine - signal transduction - solid-phase