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.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Enzymatic Synthesis of Variediene Analogs ; day:09 ; month:02 ; year:2022 ; extent:1
Chemistry - a European journal ; (09.02.2022) (gesamt 1)

Creator
Liang, Lin‐Fu
Dickschat, Jeroen S.

DOI
10.1002/chem.202200095
URN
urn:nbn:de:101:1-2022021014111020914435
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
2025-08-15T07:25:57+0200

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Associated

  • Liang, Lin‐Fu
  • Dickschat, Jeroen S.

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