The novel hydrogenase, MenJ, which selectively saturates the β-isoprene of menaquinone (MK), represents a novel virulence factor due to the fact that it is required for Mycobacterium tuberculosis survival in host macrophages (1). We are synthesizing and characterizing the physical properties of the substrates and substrate analogs. Specifically, MK-1, MK-2, MK-3, MK-4 and corresponding saturated analogs MK-1[II-H2], MK-2[II-H2], MK-3[II-H2] and MK-4[II-H2] are examples that we have made or are in progress of synthesizing. We characterize their solution structure using 2D NOESY NMR spectroscopy and electrochemistry. Access to these compounds is essential for understanding the structure-activity relationships of MenJ and the relationship of MK-structure with the phenotype of the bacterium. (1) MenI, a novel menaquinone reductase in Mycobacterium tuberculosis is required for survival in macrophages,” Ashutosh Upadhyay, Fabio Fontes, Mercedes Gonzalez-Juarrero, Michael R. McNeil, Debbie C. Crans, Mary Jackson and Dean C. Crick, ACS Central Science, 2015, ASAP DOI:10.1021/acscentsci.5b00212.

Synthesis and characterization of menaquinone (MK) analogs and other substrate analogs for the novel Mycobacterium tuberculosis hydrogenase, MenJ

251st National Meeting (2016)

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