The pyridinone-methide elimination

Rotem Perry-Feigenbaum, Phil S. Baran, Doron Shabat

Research output: Contribution to journalArticlepeer-review

Abstract

The quinone-methide elimination is a common, efficient methodology used in linkers designed to undergo self-fragmentation. Here, for the first time, we demonstrate this elimination in a pyridine ring system. Under physiological conditions, a compound constructed of a pyridine core, a reporter, and an enzymatic trigger underwent significantly faster 1,4-elimination than its parent compound with a benzene core. In addition, an AB2 self-immolative dendron based on a pyridine core released its two reporter units upon activation through 1,6- and 1,4 pyridinone-methide elimination reactions, again faster than the analogous benzene system. Increased aqueous solubility was observed with compounds based on pyridine relative to those based on benzene. The pyridinone-methide elimination could be applied as an alternative tool in designing self-immolative linkers for release of active target molecules in an aqueous environment.

Original languageEnglish
Pages (from-to)4825-4828
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number23
DOIs
StatePublished - 2009

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