Gene_locus Report for: 9agam-VibC

Boreostereum vibrans Vibralactone Cyclase

(Below N is a link to NCBI taxonomic web page and E link to ESTHER at designed phylum.)
> cellular organisms: N E > Eukaryota: N E > Opisthokonta: N E > Fungi: N E > Dikarya: N E > Basidiomycota: N E > Agaricomycotina: N E > Agaricomycetes: N E > Agaricomycetes incertae sedis: N E > Russulales: N E > Stereaceae: N E > Boreostereum: N E > Boreostereum vibrans: N E

Title: 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
Ref: Angew Chem Int Ed Engl, 59:7209, 2020 : PubMed
Abstract


ESTHER: Feng_2020_Angew.Chem.Int.Ed.Engl_59_7209
PubMedSearch: Feng 2020 Angew.Chem.Int.Ed.Engl 59 7209
PubMedID: 32050043
Gene_locus related to this paper: 9agam-VibC, stehr-Sh.112560
Inhibitor(s) related to this paper: Vibralactone

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.