Fig. 19 | The Journal of Antibiotics

Fig. 19

From: Targeting adenylate-forming enzymes with designed sulfonyladenosine inhibitors

Fig. 19

Inhibition of bacterial OSB-CoA synthetase (MenE). a MenE catalyzes adenylation of OSB (19.1) to form an OSB-AMP intermediate (19.2), which reacts with a CoA thiol nucleophile to form an OSB-CoA thioester product (19.3), en route to menaquinone (19.4). b Acyl-AMS inhibitors (19.5–19.8) mimic the OSB-AMP intermediate (19.2). Various modifications have been explored to replace the anionic aromatic carboxylate of OSB-AMS (19.7). OSB o-succinylbenzoate, TFMP-Bu trifluoromethylphenyl-4-oxobutyryl

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