title: A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.
abstract: Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography.
authors.affiliation: Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation Street, Worcester, Massachusetts 01605, USA.
authors.forename: Steven M
authors.initials: SM
authors.lastname: Pauff
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Miller
mesh_terms: D000476:Alkanesulfonates / Q000737:chemistry*; D061885:Chromophore-Assisted Light Inactivation; D005456:Fluorescent Dyes / Q000737:chemistry*; D012995:Solubility; D019265:Spectroscopy, Near-Infrared; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000476:Alkanesulfonates; D005456:Fluorescent Dyes; D014269:Trifluoroacetic Acid