Preparation of Nα-Boc 4-O-Diethylphospho-L-azatyrosine, a Regent Potentially Useful for the Synthesis of Signal Transduction Related Peptides

Bin Ye; Akira Otaka; Terrence R. Burke Jr

doi:10.1055/s-1996-5458

Synlett 1996; 1996(5): 459-460
DOI: 10.1055/s-1996-5458

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Preparation of N^α-Boc 4-O-Diethylphospho-L-azatyrosine, a Regent Potentially Useful for the Synthesis of Signal Transduction Related Peptides

Bin Ye, 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 +301-402-2275; E-mail: tburke@helix.hih.gov

Abstract

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Preparation of the phosphorylated azatyrosine analogue, 2(S)-N^α-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

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