Synthesis of 3,5-Difluorotyrosine-Containing Peptides: Application in Substrate Profiling of Protein Tyrosine Phosphatases

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...

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Bibliographic Details
Published in:Organic letters 2008-10, Vol.10 (20), p.4605-4608
Main Authors: Gopishetty, Bhaskar, Ren, Lige, Waller, Tiffany M, Wavreille, Anne-Sophie, Lopez, Miguel, Thakkar, Amit, Zhu, Jinge, Pei, Dehua
Format: Article
Language:English
Subjects:
Chromatography, High Pressure Liquid
Kinetics
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Peptides - metabolism
Protein Tyrosine Phosphatases - metabolism
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Substrate Specificity
Tyrosine - analogs & derivatives
Tyrosine - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801868a