title: 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.
authors.affiliation: Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, MA 01605, USA. Stephen.miller@umassmed.edu.
authors.forename: Adam
authors.initials: A
authors.lastname: Choi
authors.affiliation: Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, MA 01605, USA. Stephen.miller@umassmed.edu.
authors.forename: Stephen C
authors.identifier: http://orcid.org/0000-0001-7154-7757
authors.initials: SC
authors.lastname: Miller
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D004952:Esters / Q000737:chemistry* / Q000378:metabolism; D005978:Glutathione / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D013451:Sulfonic Acids / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000475:Alkenes; D004952:Esters; D011809:Quinones; D013451:Sulfonic Acids; C499744:o-thioquinone methide; D005978:Glutathione