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Preparation of an unprotected phosphotyrosine building block and its application in solid-phase synthesis of phosphopeptides

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Abstract

A new and facile synthesis of tyrosine phosphorylated peptides has been developed. Nα-Fmoc-TyrtBu)-OPfp was treated with TFA, phosphorylated with phosphorous oxychloride and the resulting phosphoric acid dichloride was hydrolysed to give Nα-Fmoc-Tyr(PO3H32)-OPfp 1 in an overall yield of 98%. Compound 1 was used in solid-phase peptide synthesis of phosphopeptides 2, 3 and 4, which are fragments of murine adipocyte lipid binding protein. The advantage of using the Pfp ester was the absence of pyrophosphates and other byproducts.

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Authors and Affiliations

  1. Carlsberg Laboratory, Department of Chemistry, Gamle Carlsberg Vej 10, DK-2500, Valby, Copenhagen, Denmark

    Christian Krog-Jensen, Mette K. Christensen & Morten Meldal

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  1. Christian Krog-Jensen
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  2. Mette K. Christensen
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  3. Morten Meldal
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Krog-Jensen, C., Christensen, M.K. & Meldal, M. Preparation of an unprotected phosphotyrosine building block and its application in solid-phase synthesis of phosphopeptides. Letters in Peptide Science 6, 193–197 (1999). https://doi.org/10.1023/A:1008839805390

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