Enzymatic synthesis of psilocybin, the ingredient of magic mushrooms
Little fungi pack a punch: “Magic mushrooms” of the Psilocybe species produce psychoactive compounds that alter perception when ingested. Recently, the effects on the neuronal system caused by their ingredient psilocybin have attracted the interest of pharmacologists.
German scientists have now identified four of the enzymes responsible for the biosynthesis of psilocybin. In the journal Angewandte Chemie, they describe the biosynthetic pathway and introduce a synthetic route that could form the basis of biotechnological production.
For centuries, Central American cultures considered Psilocybe mushrooms to be divine and used them for spiritual purposes. More recently, they have been called magic mushrooms and used for their hallucinogenic effects. These mushroom drugs may soon also be in use as pharmaceuticals that treat the existential anxiety of advanced-stage cancer patients, depression, and nicotine addiction.
Their effects stem from tryptamines, which are chemical derivatives of the amino acid L-tryptophan and structural relatives of the neurotransmitters serotonin and melatonin. Among these, psilocybin is the primary chemical mushroom component. Psilocybin is an inactive precursor that is rapidly activated when consumed: splitting off a phosphate group results in the actual active ingredient, psilocin.
Although the structure of psilocybin has been known for about 60 years, it has not been possible to decode the enzymatic basis of its biosynthesis. Researchers working with Dirk Hoffmeister at the Friedrich Schiller University of Jena have now figured this out.
They have identified the four enzymes that transform the amino acidy L-tryptophan into psilocybin. Using genetic technology, the researchers were able to produce the enzymes in bacterial and mould fungi cultures and characterize them.
Based on this knowledge, they were also able to clarify the biosynthetic production route, which is different than previously supposed. In the first step of the biosynthesis, an unsusual type of tryptophan decarboxylase splits the carboxyl group off of the amino acid L-tryptophan.
A monooxygenase then introduces an alcohol group, to which a kinase subsequently adds a phosphate group. Finally, a methyl transferase adds two methyl groups stepwise to the amino group.
Starting with 4-hydroxy-L-tryptophan and using three of the four fungal enzymes, the scientists were able to enzymatically synthesize psilocybin by a simple method in a combined reaction. Given the pharmaceutical industry's renewed interest in psilocybin, these results may lay the foundation for its biotechnological production.
Dirk Hoffmeister is Full Professor of Pharmaceutical Microbiology at the University of Jena and the Leibniz Institute for Natural Product Research and Infection Biology (Hans-Knöll-Institute) in Jena. His research focuses on the genetic and biochemical bases of bioactive component synthesis in fungi.
Author: Dirk Hoffmeister, Friedrich-Schiller-Universität Jena (Germany), http://www.pharmazie.uni-jena.de/Institut/Pharmazeutische+Mikrobiologie/Prof_+Dr_+Dirk+Hoffmeister.html
Title: Enzymatic Synthesis of Psilocybin
Angewandte Chemie International Edition
Permalink to the original article: https://doi.org/10.1002/anie.201705489 – Please use in your news piece to make sure altmetric.com picks it up and a link to your piece is shown on the journal's website.
Copy free of charge. We would appreciate a transcript of your article or a reference to it.
The original article is available from our online pressroom at http://pressroom.angewandte.org.
Contact: Editorial office: firstname.lastname@example.org
To be removed from this list, please e-mail us.
Angewandte Chemie is a journal of the Gesellschaft Deutscher Chemiker (German Chemical Society, GDCh) and is published by Wiley-VCH. It is one of the prime chemistry journals in the world. Celebrate the society's 150th anniversary with us and eminent speakers, among them four Nobel Laureates.
Angewandte Chemie International Edition, Postfach 101161, 69451 Weinheim, Germany.
Dirk Hoffmeister | Gesellschaft Deutscher Chemiker e.V.
Zebrafish's near 360 degree UV-vision knocks stripes off Google Street View
22.06.2018 | University of Sussex
New cellular pathway helps explain how inflammation leads to artery disease
22.06.2018 | Cedars-Sinai Medical Center
In a recent publication in the renowned journal Optica, scientists of Leibniz-Institute of Photonic Technology (Leibniz IPHT) in Jena showed that they can accurately control the optical properties of liquid-core fiber lasers and therefore their spectral band width by temperature and pressure tuning.
Already last year, the researchers provided experimental proof of a new dynamic of hybrid solitons– temporally and spectrally stationary light waves resulting...
Scientists from the University of Freiburg and the University of Basel identified a master regulator for bone regeneration. Prasad Shastri, Professor of...
Moving into its fourth decade, AchemAsia is setting out for new horizons: The International Expo and Innovation Forum for Sustainable Chemical Production will take place from 21-23 May 2019 in Shanghai, China. With an updated event profile, the eleventh edition focusses on topics that are especially relevant for the Chinese process industry, putting a strong emphasis on sustainability and innovation.
Founded in 1989 as a spin-off of ACHEMA to cater to the needs of China’s then developing industry, AchemAsia has since grown into a platform where the latest...
The BMBF-funded OWICELLS project was successfully completed with a final presentation at the BMW plant in Munich. The presentation demonstrated a Li-Fi communication with a mobile robot, while the robot carried out usual production processes (welding, moving and testing parts) in a 5x5m² production cell. The robust, optical wireless transmission is based on spatial diversity; in other words, data is sent and received simultaneously by several LEDs and several photodiodes. The system can transmit data at more than 100 Mbit/s and five milliseconds latency.
Modern production technologies in the automobile industry must become more flexible in order to fulfil individual customer requirements.
An international team of scientists has discovered a new way to transfer image information through multimodal fibers with almost no distortion - even if the fiber is bent. The results of the study, to which scientist from the Leibniz-Institute of Photonic Technology Jena (Leibniz IPHT) contributed, were published on 6thJune in the highly-cited journal Physical Review Letters.
Endoscopes allow doctors to see into a patient’s body like through a keyhole. Typically, the images are transmitted via a bundle of several hundreds of optical...
13.06.2018 | Event News
08.06.2018 | Event News
05.06.2018 | Event News
22.06.2018 | Materials Sciences
22.06.2018 | Earth Sciences
22.06.2018 | Life Sciences