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Biocatalytic C-H Activation of the JAK inhibitor Ruxolitinib

Biocatalytic C-H activation of the JAK inhibitor ruxolitinib

Ruxo metabolties diagram

Presented at: Drug Discovery Chemistry meeting, 2018, San Diego, USA

The first-in-class JAK inhibitor, ruxolitinib (trade names Jakafi® and Jakavi®), is primarily metabolized to a complex mixture of stereoisomeric cyclopentyl hydroxyl and keto metabolites. Application of Hypha’s microbial-based biocatalytic C-H bond activation to ruxolitinib resulted in the production of an array of hydroxylated and further oxidized keto metabolites, many of which corresponded to circulating human metabolites. All possible oxidized isomers of the aliphatic cyclopentyl moiety were derived from a variety of microbial species which were readily scaled up, enabling efficient production of stereoisomer metabolite standards for structural characterization and bioanalytical monitoring.

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