Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209

Reference

Title : A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone - Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209
Author(s) : Feng KN , Yang YL , Xu YX , Zhang Y , Feng T , Huang SX , Liu JK , Zeng Y
Ref : Angew Chem Int Ed Engl , 59 :7209 , 2020
Abstract :

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 via an oxidative ring-expansion prior to an intramolecular cyclization. Here, 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 catalytic Ser-His-Asp 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 b-lactone. This presents a naturally occurring new enzyme 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.

PubMedSearch : Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209
PubMedID: 32050043
Gene_locus related to this paper: 9agam-VibC , stehr-Sh.112560

Related information

Inhibitor Vibralactone
Substrate 1,5-Seco-vibralactone
Gene_locus 9agam-VibC    stehr-Sh.112560
Structure 6KD0

Citations formats

Feng KN, Yang YL, Xu YX, Zhang Y, Feng T, Huang SX, Liu JK, Zeng Y (2020)
A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic beta-Lactone in Vibralactone
Angew Chem Int Ed Engl 59 :7209

Feng KN, Yang YL, Xu YX, Zhang Y, Feng T, Huang SX, Liu JK, Zeng Y (2020)
Angew Chem Int Ed Engl 59 :7209