Tetrahedron

Fluorescence turn-on probe for biothiols: intramolecular hydrogen bonding effect on the Michael reaction

HJ Ha, DH Yoon, S Park, HJ Kim

Index: Ha, Hyun-Joon; Yoon, Doo-Ha; Park, Seokan; Kim, Hae-Jo Tetrahedron, 2011 , vol. 67, # 40 p. 7759 - 7762

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Citation Number: 14

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 ...