ArticleThe Journal of organic chemistry2013
A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Synthesis and Optimization of Ethylenediamine-Based Zwitterion on Polymer Side Chain for Recognizing Narrow Tumorous pH Windows.Biomacromolecules · 2024Article
- Protected Poly(3-sulfopropyl methacrylate) Copolymers: Synthesis, Stability, and Orthogonal Deprotection.ACS polymers Au · 2022Article
- Metal- and Reagent-Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi-Component Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Extensive Structure-Activity Relationship Study of Albicidin's C-Terminal Dipeptidic p-Aminobenzoic Acid Moiety.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Reductively-labile sulfonate ester protecting groups that are rapidly cleaved by physiological glutathione.Organic & biomolecular chemistry · 2017Article
- Synthesis and Solution-Phase Characterization of Sulfonated Oligothioetheramides.Macromolecules · 2017Article
- Paradigms of sulfotransferase catalysis: the mechanism of SULT2A1.The Journal of biological chemistry · 2014Article
- Bright building blocks for chemical biology.ACS chemical biology · 2014Review
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Authors and funding
2 authors.
Funding
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.
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Registered trials
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