title: Trichloroethyl group as a protecting group for sulfonates and its application to the synthesis of a disulfonate analog of the tyrosine sulfated PSGL-1(43-50) peptide.
abstract: The trichloroethyl (TCE) group is shown to be a viable protecting group for sulfonates. TCE-protected sulfonates were found to be particularly stable to acid, a key characteristic that led to a straightforward enantioselective synthesis of l-FmocPhe(p-CH(2)SO(3)TCE)OH. This was used as a building block for the solid phase synthesis of an octapeptide corresponding to P-selectin glycoprotein ligand-1 residues 43-50 (PSGL-1(43-50)) in which sulfotyrosine residues 46 and 48 were replaced with (sulfonomethyl)phenylalanine (SmP), an important hydrolytically stable sulfotyrosine mimic.
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario, Canada, N2L 3G1.
authors.forename: Ahmed M
authors.initials: AM
authors.lastname: Ali
authors.forename: Bryan
authors.initials: B
authors.lastname: Hill
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor