Profiling sulfonate ester stability: identification of complementary protecting groups for sulfonates.
Sulfonation is prized for its ability to impart water-solubility to hydrophobic molecules such as dyes. This modification is usually performed as a final step, since sulfonated molecules are poorly soluble in most organic solvents, which complicates their synthesis and purification. This work compares the intrinsic lability of different sulfonate esters, identifying new sulfonate protecting groups and mild, selective cleavage conditions.
Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St., Worcester, Massachusetts 01605, USA. stephen.miller@umassmed.edu
Stephen C
SC
Miller
D000476:Alkanesulfonates / Q000737:chemistry*; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012995:Solubility; D012997:Solvents / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000737:chemistry*
D000476:Alkanesulfonates; D004952:Esters; D012997:Solvents; D013451:Sulfonic Acids