Synthesis of L-2,3,5,6-tetrafluoro-4-(phosphonomethyl)phenylalanine, a novel non-hydrolyzable phosphotyrosine mimetic and L-4-(phosphonodifluoromethyl)phenylalanine

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Abstract

A new non-hydrolyzable phosphotyrosine analogue, L-F4Pmp and its N-Fmoc protected derivative were prepared by using an enantioselective synthetic pathway with camphor sultam as chiral auxiliary. The side chain pKa2(6.9) of L-F4Pmp was determined A new synthesis of L-F4Pmp was also described.

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Liu, W. Q., Roques, B. P., & Garbay, C. (1997). Synthesis of L-2,3,5,6-tetrafluoro-4-(phosphonomethyl)phenylalanine, a novel non-hydrolyzable phosphotyrosine mimetic and L-4-(phosphonodifluoromethyl)phenylalanine. Tetrahedron Letters, 38(8), 1389–1392. https://doi.org/10.1016/S0040-4039(97)00027-0

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