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Nα-Fmoc-O,O-(dimethylphospho)-L-tyrosine fluoride: A convenient building block for the solid-phase synthesis of phosphotyrosyl peptides

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Abstract

Fmoc-O,O-(dimethylphospho)-L-tyrosine was converted into stable Fmoc-O,O-(dimethylphospho)-L-tyrosine fluoride by means of (diethylamino)sulfur trifluoride or cyanuric fluoride. This building block was used for efficient coupling of phosphotyrosine to the adjacent sterically hindered amino acid Aib or Ac6c in model peptide sequences as well as for the synthesis of the ‘difficult’ phosphotyrosine peptide Stat91695-708. The phosphate methyl groups were cleaved on solid phase after peptide assembly by means of trimethylsilyl iodide in MeCN.

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  1. Oncology Research, Novartis Pharma AG, CH-4002, Basel, Switzerland

    Heinz Fretz

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  1. Heinz Fretz
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Fretz, H. Nα-Fmoc-O,O-(dimethylphospho)-L-tyrosine fluoride: A convenient building block for the solid-phase synthesis of phosphotyrosyl peptides. Letters in Peptide Science 4, 171–176 (1997). https://doi.org/10.1023/A:1008806907085

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