Synthesis of 3,5-difluorotyrosine-containing peptides: application in substrate profiling of protein tyrosine phosphatases

  • Org Lett. 2008 Oct 16;10(20):4605-8. doi: 10.1021/ol801868a.
Bhaskar Gopishetty  1 ,  Lige Ren ,  Tiffany M Waller ,  Anne-Sophie Wavreille ,  Miguel Lopez ,  Amit Thakkar ,  Jinge Zhu ,  Dehua Pei
Affiliations
  • 1. Department of Chemistry and Ohio State Biochemistry Program, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
PMID: 18798640 DOI: 10.1021/ol801868a
Abstract

Fully protected 3,5-difluorotyrosine (F2Y), Fmoc-F2Y(tBu)-OH, is efficiently prepared by a chemoenzymatic process and incorporated into individual peptides and combinatorial peptide libraries. The F2Y-containing peptides display kinetic properties toward Protein tyrosine phosphatases (PTPs) similar to their corresponding tyrosine-containing counterparts but are resistant to Tyrosinase action. These properties make F2Y a useful tyrosine surrogate during peptide library screening for optimal PTP substrates.

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