University of Massachusetts Medical School Faculty Publications
Title
A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore
UMMS Affiliation
Department of Biochemistry and Molecular Pharmacology
Publication Date
2013-01-18
Document Type
Article
Subjects
Alkanesulfonates; Chromophore-Assisted Light Inactivation; Fluorescent Dyes; Solubility; Spectroscopy, Near-Infrared; Trifluoroacetic Acid
Disciplines
Biochemistry | Organic Chemistry
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.
DOI of Published Version
10.1021/jo302065u
Source
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
Related Resources
Journal/Book/Conference Title
The Journal of organic chemistry
PubMed ID
23167708
Repository Citation
Pauff SM, Miller SC. (2013). A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore. University of Massachusetts Medical School Faculty Publications. https://doi.org/10.1021/jo302065u. Retrieved from https://escholarship.umassmed.edu/faculty_pubs/204