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A Synthetic Methodology Toward Pyrrolo[2,3- b]pyridones for GC Base Pair Recognition. | LitMetric

A Synthetic Methodology Toward Pyrrolo[2,3- b]pyridones for GC Base Pair Recognition.

Org Lett

Faculty of Chemistry , University of Duisburg-Essen , Universitätsstraße 7, 45117 Essen , Germany.

Published: November 2018

Flexible synthetic access to a novel biarylic GC binding motif is presented, consisting of a pyridone connected to a fused pyrrolo[2,3- b]pyridone. Extensive molecular modeling led to an optimized design with perfect complementarity to the Hoogsteen site inside DNA's major groove. A wide range of functional elements can be introduced by minor modifications of the synthetic strategy. Our approach relies on mild Pd-catalyzed coupling reactions, featuring a triple heterohalogenated orthogonally addressable pyridine as a key intermediate.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b03111DOI Listing

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