Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 43, Pages 23412-23418Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107619
Keywords
biocatalysis; methyl transferase; natural products; physostigmine; SAM recycling
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Funding
- state of North Rhine Westphalia (NRW)
- European Regional Development Fund (EFRE) [34-EFRE-0300096, 34-EFRE-0300097]
- Heinrich Heine University Dusseldorf
- Forschungszentrum Julich GmbH
- Projekt DEAL
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The study characterized in detail the biochemical properties and substrate scope of the SAM-dependent methyl transferase PsmD from Streptomyces griseofuscus, and successfully achieved preparative scale enzymatic methylation for three selected substrates.
Enantioselective synthesis of bioactive compounds bearing a pyrroloindole framework is often laborious. In contrast, there are several S-adenosyl methionine (SAM)-dependent methyl transferases known for stereo- and regioselective methylation at the C3 position of various indoles, directly leading to the formation of the desired pyrroloindole moiety. Herein, the SAM-dependent methyl transferase PsmD from Streptomyces griseofuscus, a key enzyme in the biosynthesis of physostigmine, is characterized in detail. The biochemical properties of PsmD and its substrate scope were demonstrated. Preparative scale enzymatic methylation including SAM regeneration was achieved for three selected substrates after a design-of-experiment optimization.
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