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Technical Note:
1. This di-sulfonated building block is recommended for post-synthetic water-solubilization of hydrophobic, molecules for applications in biological media, especially organic dyes, fluorophores, azo dyes[1], bodipy[2], coumarin[3]and xanthene dyes[4].
This includes organic supramolecular compounds such as cryptophanes[5], through aminolysis reactions of activated esters, activated carbamates (or carbonates) and isothiocyanates. Such reactions can be performed either in aqueous media
(Schotten-Baumann conditions), or in anhydrous organic media (by converting this di-sulfonated taurine analog into the
corresponding tributylammonium or tetrabutylammonium salt[2,4]). Such methodology is also applicable for sulfonation of
biomolecules such as peptides and nucleic acids, for fine-tuning their net electric charge[6].
A further derivatization of this unusual amine with 3-azidopropanoic acid, 3-mercaptopropanoic acid, or 4-pentynoic acid,
provides a di-sulfonated linker that is reactive in either “click reactions (1,3-dipolar cycloadditions), SNAr or Sonogashira
cross-couplings[1].
References:
1. Chem.-Eur., J., 2013, 19, 1686.
2. New J. Chem., 2013, 37, 1016.
3. Dyes Pigm., 2014, 110, 270.
4. Tetrahedron Lett., 2010, 51, 3304.
5. Chem. Commun., 2011, 47, 9702.
6. Bioconjugate Chem., 2014, 25, 1000.
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