Enzymatic Route toward 6-Methylated Baeocystin and Psilocybin

Janis Fricke, Alexander Sherwood, Robert Kargbo, Andrew Orry, Felix Blei, Andreas Naschberger, Bernhard Rupp, Dirk Hoffmeister

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Psilocybin and its direct precursor baeocystin are indole alkaloids of psychotropic Psilocybe mushrooms. The pharmaceutical interest in psilocybin as a treatment option against depression and anxiety is currently being investigated in advanced clinical trials. Here, we report a biocatalytic route to synthesize 6-methylated psilocybin and baeocystin from 4-hydroxy-6-methyl-l-tryptophan, which was decarboxylated and phosphorylated by the Psilocybe cubensis biosynthesis enzymes PsiD and PsiK. N-Methylation was catalyzed by PsiM. We further present an in silico structural model of PsiM that revealed a well-conserved SAM-binding core along with peripheral nonconserved elements that likely govern substrate preferences.
Original languageEnglish (US)
Pages (from-to)2824-2829
Number of pages6
JournalChemBioChem
Volume20
Issue number22
DOIs
StatePublished - Nov 18 2019
Externally publishedYes

Bibliographical note

Generated from Scopus record by KAUST IRTS on 2023-02-15

ASJC Scopus subject areas

  • General Medicine

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