Synthesis of protected L-4-[sulfono(difluoromethyl)phenylalanine and its incorporation into a peptide.
[reaction: see text] A protected form of L-4-[sulfono(difluoromethyl)]phenylalanine (F(2)Smp), a novel non-hydrolyzable phospho- and sulfotyrosine mimetic, was synthesized via electrophilic fluorination of a benzylic sulfonate followed by a Pd-catalyzed cross-coupling reaction between the fluorinated sulfonate and the zincate of protected iodoalanine. F(2)Smp was incorporated into a peptide using solid-phase peptide synthesis techniques.
Liu
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Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario N2L 3G1, Canada.
Dockendorff
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C
Taylor
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SD
D020650:Combinatorial Chemistry Techniques; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D010455:Peptides / Q000138:chemical synthesis*; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry*; D014443:Tyrosine / Q000031:analogs & derivatives*
D004791:Enzyme Inhibitors; D010455:Peptides; C005662:tyrosine O-sulfate; D014443:Tyrosine; D010649:Phenylalanine