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 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.
Gopishetty
Bhaskar
B
Department of Chemistry and Ohio State Biochemistry Program, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
Ren
Lige
L
Waller
Tiffany M
TM
Wavreille
Anne-Sophie
AS
Lopez
Miguel
M
Thakkar
Amit
A
Zhu
Jinge
J
Pei
Dehua
D
D002851:Chromatography, High Pressure Liquid; D007700:Kinetics; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D017027:Protein Tyrosine Phosphatases / Q000378:metabolism*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013379:Substrate Specificity; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
D010455:Peptides; C025200:3,5-difluorotyrosine; D014443:Tyrosine; D017027:Protein Tyrosine Phosphatases
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