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Reductively-labile sulfonate ester protecting groups that are rapidly cleaved by physiological glutathione.

ABSTRACT: Sulfonates are frequently used to endow water solubility on hydrophobic molecules, but the repertoire of sulfonate protecting groups remains limited. Here we describe the first sulfonate esters that can be unmasked by the mild reducing conditions found in live mammalian cells. Self-immolative cleavage releases the sulfonate and the two-electron reduction product of a thioquinone methide.

SUBMITTER: Choi A

PROVIDER: S-EPMC6563934 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Reductively-labile sulfonate ester protecting groups that are rapidly cleaved by physiological glutathione.

Choi Adam A Miller Stephen C SC

Organic & biomolecular chemistry 20170201 6

Sulfonates are frequently used to endow water solubility on hydrophobic molecules, but the repertoire of sulfonate protecting groups remains limited. Here we describe the first sulfonate esters that can be unmasked by the mild reducing conditions found in live mammalian cells. Self-immolative cleavage releases the sulfonate and the two-electron reduction product of a thioquinone methide. ...[more]

PMID: 28116407

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