A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore
Department of Biochemistry and Molecular Pharmacology
Medical Subject Headings
Alkanesulfonates; Chromophore-Assisted Light Inactivation; Fluorescent Dyes; Solubility; Spectroscopy, Near-Infrared; Trifluoroacetic Acid
Biochemistry | Organic Chemistry
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.
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Citation: J Org Chem. 2013 Jan 18;78(2):711-6. doi: 10.1021/jo302065u. Epub 2012 Dec 13. Link to article on publisher's site
Pauff, Steven M. and Miller, Stephen C., "A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore" (2013). University of Massachusetts Medical School Faculty Publications. 204.