Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase‐Enhanced Reactions
Felix Blei, Florian Baldeweg, Janis Fricke, Dirk Hoffmeister
Chemistry - A European Journal May 11, 2018 DOI: 10.1002/chem.201801047 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Psilocybin |
| Keywords | Biochemistry Stereochemistry Pharmacology Hallucinogen Alkaloids |
| Citations | 51 |
| Key findings | An enhanced enzymatic route using TrpB produces psilocybin from cheaper substrates (4-hydroxyindole and L-serine) and also yields isonorbaeocystin and serotonin. |
Abstract
Abstract 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.
Comparable studies
Other experimental studies on psilocybin, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Psilocybin induces schizophrenia-like psychosis in humans via a serotonin-2 agonist action Healthy human volunteers | 1998 | Experimental study | |
| Validation of the revised Mystical Experience Questionnaire in experimental sessions with psilocybin Participants in controlled laboratory experiments receiving a moderate to high oral... | 2015 | Validation study using pooled data from five laboratory experiments | n = 184 |
| Broadband Cortical Desynchronization Underlies the Human Psychedelic State Healthy human participants | 2013 | Experimental study | |
| Long-term follow-up of psilocybin-assisted psychotherapy for psychiatric and existential distress in patients with life-threatening cancer Participants with cancer-related psychiatric distress who completed a parent randomized... | 2020 | Long-term within-subjects follow-up analysis | n = 15 |
| Enzymatic Synthesis of Psilocybin | 2017 | Laboratory study |
Citations in the library
Cited by 37
- Diversity, biology, and history of psilocybin-containing fungi: Suggestions for research and technological development. Fungal biology April 1, 2022
- In vivo production of psilocybin in E. coli Metabolic Engineering September 21, 2019
- Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis Drug Testing and Analysis October 29, 2020
- Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin Chemistry - A European Journal February 26, 2020
- Genetic Survey of Psilocybe Natural Products ChemBioChem May 18, 2022
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Cites 12
- Pilot Study of Psilocybin Treatment for Anxiety in Patients With Advanced-Stage Cancer Archives of General Psychiatry September 7, 2010
- Pilot study of the 5-HT2AR agonist psilocybin in the treatment of tobacco addiction Journal of Psychopharmacology September 11, 2014
- Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose?effect study Psychopharmacology March 1, 2004
- Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen Helvetica Chimica Acta 1959
- Enzymatic Synthesis of Psilocybin Angewandte Chemie International Edition August 1, 2017
and 7 more in the library