3 years ago

Mechanisms of the Diterpene Cyclases β-Pinacene Synthase from Dictyostelium discoideum and Hydropyrene Synthase from Streptomyces clavuligerus

Mechanisms of the Diterpene Cyclases β-Pinacene Synthase from Dictyostelium discoideum and Hydropyrene Synthase from Streptomyces clavuligerus
Tobias G. Köllner, Patrick Rabe, Jeroen S. Dickschat, Feng Chen, Xinlu Chen, Jan Rinkel
Two diterpene cyclases, one from the social amoeba Dictyostelium discoideum and the other from the bacterium Streptomyces clavuligerus, with products containing a Z-configured double bond between the original C2 and C3 of geranylgeranyl diphosphate, were extensively investigated for their mechanisms through isotopic labelling experiments. The participation of geranyllinalyl diphosphate, in analogy to the role of linalyl and nerolidyl diphosphate for mono- and sesquiterpene biosynthesis, as an intermediate towards diterpenes with a Z-configured C2=C3 double bond is discussed. The cyclisation mechanisms of two diterpene cyclases, one from the social amoeba Dictyostelium discoideum and the other from the bacterium Streptomyces clavuligerus, were investigated by isotopic labelling experiments. Substrate isomerization by allylic transposition of diphosphate, in analogy to a well established mechanism for mono- and sesquiterpene biosynthesis, takes part in the formation of products with Z-configured double bonds.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702704

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