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Enzymatic Synthesis of Variediene Analogs.

ABSTRACT: Five analogs of dimethylallyl diphosphate (DMAPP) with additional or shifted Me groups were converted with isopentenyl diphosphate (IPP) and the fungal variediene synthase from Aspergillus brasiliensis (AbVS). These enzymatic reactions resulted in the formation of several new terpene analogs that were isolated and structurally characterised by NMR spectroscopy. Several DMAPP analogs showed a changed reactivity giving access to compounds with unusual skeletons. Their formation is mechanistically rationalised and the absolute configurations of all obtained compounds were determined through a stereoselective deuteration strategy, revealing absolute configurations that are analogous to that of the natural enzyme product variediene.

SUBMITTER: Liang LF

PROVIDER: S-EPMC9305479 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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Enzymatic Synthesis of Variediene Analogs.

Liang Lin-Fu LF Dickschat Jeroen S JS

Chemistry (Weinheim an der Bergstrasse, Germany) 20220209 15

Five analogs of dimethylallyl diphosphate (DMAPP) with additional or shifted Me groups were converted with isopentenyl diphosphate (IPP) and the fungal variediene synthase from Aspergillus brasiliensis (AbVS). These enzymatic reactions resulted in the formation of several new terpene analogs that were isolated and structurally characterised by NMR spectroscopy. Several DMAPP analogs showed a changed reactivity giving access to compounds with unusual skeletons. Their formation is mechanistically ...[more]

PMID: 35084065

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