Structural highlights
Publication Abstract from PubMed
Vibralactone is isolated from the basidiomycete fungus Boreostereum vibrans as one of the strongest lipase inhibitors. Its unusual beta-lactone-fused bicycle is derived from an aryl ring moiety by an oxidative ring-expansion prior to an intramolecular cyclization. Herein, we report the discovery of the cyclase VibC which belongs to the alpha/beta-hydrolase superfamily and is involved in the vibralactone biosynthesis. Biochemical and crystal studies suggest that VibC may catalyze an aldol or an electrocyclic reaction initiated by the Ser-His-Asp catalytic triad. For the aldol and pericyclic chemistry in living cells, VibC is a unique hydrolase performing the carbocycle formation of an oxepinone to a fused bicyclic beta-lactone. This presents a naturally occurring, new enzymatic reaction in both aldol and hydrolase (bio)chemistry that will guide future exploitation of these enzymes in synthetic biology for chemical-diversity expansion of natural products.
A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone.,Feng KN, Yang YL, Xu YX, Zhang Y, Feng T, Huang SX, Liu JK, Zeng Y Angew Chem Int Ed Engl. 2020 Apr 27;59(18):7209-7213. doi:, 10.1002/anie.202000710. Epub 2020 Mar 9. PMID:32050043[1]
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.
References
- ↑ Feng KN, Yang YL, Xu YX, Zhang Y, Feng T, Huang SX, Liu JK, Zeng Y. A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic β-Lactone in Vibralactone. Angew Chem Int Ed Engl. 2020 Apr 27;59(18):7209-7213. PMID:32050043 doi:10.1002/anie.202000710
