Journal
CHEMBIOCHEM
Volume 20, Issue 22, Pages 2824-2829Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201900358
Keywords
baeocystin; biosynthesis; enzymes; methyltransferase; psilocybin
Funding
- Austrian Science Fund FWF [P 28395] Funding Source: Medline
- Deutsche Forschungsgemeinschaft [HO 2515/7-1] Funding Source: Medline
- Austrian Science Fund (FWF) [P28395] Funding Source: Austrian Science Fund (FWF)
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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.
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