Improved synthesis of [p-phosphono and p-sulfo] methylphenylalanine. Resolution of [p-phosphono-, p-sulfo-, p-car☐ y-and pN-hydroxycar☐ amido-] …

C Garbay-Jaureguiberry, I McCort-Tranchepain…

Index: Garbay-Jaureguiberry; McCort-Tranchepain; Barbe; Ficheux; Roques Tetrahedron Asymmetry, 1992 , vol. 3, # 5 p. 637 - 650

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Citation Number: 27

Abstract

Abstract To analyse the role of post-translational phosphorylation and sulfation of tyrosine in peptides and proteins, we recently synthesized the new amino acids, p (CH 2 PO 3 H 2) Phe and p (CH 2 SO 3 H) Phe (D, L mixtures) as chemically and enzymatically stable analogs of (O-phospho) and (O-sulfo)-tyrosine. Here, we report improved syntheses of these amino acids and of their N-Boc protected derivatives for use in solid-phase peptide synthesis. A ...