Preparation of an unprotected phosphotyrosine building block and its application in solid-phase synthesis of phosphopeptides
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A new and facile synthesis of tyrosine phosphorylated peptides has been developed.N α-Fmoc-Tyr(tBu)-OPfp was treated with TFA, phosphorylated with phosphorous oxychloride and the resulting phosphoric acid dichloride was hydrolysed to giveN α-Fmoc-Tyr(PO3H2)-OPfp1 in an overall yield of 98%. Compound1 was used in solid-phase peptide synthesis of phosphopeptides2, 3 and4, which are fragments of murine adipocyte lipid binding protein. The advantage of using the Pfp ester was the absence of pyrophosphates and other byproducts.
Key wordskinase substrate non-protected phosphate phosphate protection phosphorous oxychloride
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