Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 40, Pages 10028-10031Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801047
Keywords
alkaloid; biosynthesis; enzymes; psilocybin; tryptophan synthase
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Funding
- Excellence Graduate School Jena School for Microbial Communication (JSMC)
- Deutsche Forschungsgemeinschaft [HO2515/7-1]
- DFG Collaborative Research Center ChemBioSys [1127]
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Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) is the main alkaloid of the fungal genus Psilocybe, the so-called magic mushrooms. The pharmaceutical interest in this psychotropic natural product as a future medication to treat depression and anxiety is strongly re-emerging. Here, we present an enhanced enzymatic route of psilocybin production by adding TrpB, the tryptophan synthase of the mushroom Psilocybe cubensis, to the reaction. We capitalized on its substrate flexibility and show psilocybin formation from 4-hydroxyindole and l-serine, which are less cost-intensive substrates, compared to the previous method. Furthermore, we show enzymatic production of 7-phosphoryloxytryptamine (isonorbaeocystin), a non-natural congener of the Psilocybe alkaloid norbaeocystin (4-phosphoryloxytryptamine), and of serotonin (5-hydroxytryptamine) by means of the same in vitro approach.
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