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Synlett 1998; 1998(4): 428-430
DOI: 10.1055/s-1998-3131
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Preparation of Phospho-l-Azatyrosine Suitably Protected for the Synthesis of Signal Transduction Related Peptides. A Correction

Zhu-Jun Yao* , Bin Ye, Kengo Miyoshi, Akira Otaka, Terrence R. Burke, Jr.
  • *Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, National Institutes of Health, Building 37, Room 5C06, Bethesda, Maryland 20892, U.S.A.; Fax + 301-402-22 75; E-mail: tburke@helix.nih.gov
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Publication Date:
31 December 2000 (online)

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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

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