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Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis.

ABSTRACT: A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chemical conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chemical library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

SUBMITTER: Li JY

PROVIDER: S-EPMC6706801 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis.

Li Jian-Yuan JY Miklossy Gabriella G Modukuri Ram K RK Bohren Kurt M KM Yu Zhifeng Z Palaniappan Murugesan M Faver John C JC Riehle Kevin K Matzuk Martin M MM Simmons Nicholas N

Bioconjugate chemistry 20190731 8

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chemical conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chemical library synthesis and subsequent discovery of enriched features fr ...[more]

PMID: 31329429

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