Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220421 | Tetrahedron | 2011 | 4 Pages |
Abstract
Weakly fluorescent coumarinyl enones are rapidly transformed into strongly fluorescent molecules through the Michael addition reaction of a thiol group, where an intramolecular hydrogen bond plays a critical role in the reaction rate. The molecular probe (3) with an ortho hydroxyl group to a carbonyl group exhibits a rapid response toward GSH owing to the stabilization of the possible oxyanion intermediate by a preferable intramolecular hydrogen bond. Probe 1 with an o-hydroxyl group also showed a moderately enhanced reaction rate with GSH and soluble in HEPES buffer to exhibit a highly selective and sensitive fluorescence turn-on response toward biothiols.
Graphical abstractDownload full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hyun-Joon Ha, Doo-Ha Yoon, Seokan Park, Hae-Jo Kim,