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. Author manuscript; available in PMC: 2017 Dec 14.
Published in final edited form as: J Am Chem Soc. 2016 Nov 30;138(49):16024–16036. doi: 10.1021/jacs.6b09748

Figure 10.

Figure 10

FabA-isomerization mechanism and proposed mechanism of vinylogous dehydration by curacin dehydratases J and H. The two events share a common intermediary vinylogous enolate and only differ only in the final re-protonation or elimination. Site-directed mutagenesis of the catalytic dyad indicates that both the canonical histidine and aspartic residues are the general base and acid, respectively. FabA (Escherichia coli β-hydroxydecanoyl thiol ester dehydrase) catalyzes elimination and bond isomerization in fatty acid biosynthesis.