Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase-Enhanced Reactions

Chemistry : a European Journal
Felix BleiDirk Hoffmeister

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.

References

Jun 1, 1974·European Journal of Biochemistry·D H Wolf, M Hoffmann
Nov 15, 1958·Experientia·A HOFMANNF TROXLER
Feb 6, 2004·Pharmacology & Therapeutics·David E Nichols
Jun 25, 2004·Nucleic Acids Research·Mario StankeBurkhard Morgenstern
Dec 1, 2006·Chemical Communications : Chem Comm·Rebecca J M Goss, Philip L A Newill
May 20, 2008·Trends in Biochemical Sciences·Michael F DunnIlme Schlichting
Aug 6, 2008·Current Opinion in Chemical Biology·Gavin J WilliamsJon S Thorson
Sep 8, 2010·Archives of General Psychiatry·Charles S GrobGeorge R Greer
Sep 13, 2014·Journal of Psychopharmacology·Matthew W JohnsonRoland R Griffiths
Jan 13, 2015·Current Opinion in Chemical Biology·Carl A DenardHuimin Zhao
Nov 11, 2015·Proceedings of the National Academy of Sciences of the United States of America·Andrew R BullerFrances H Arnold
Jun 30, 2016·Journal of the American Chemical Society·Michael HergerFrances H Arnold
Dec 23, 2016·Chembiochem : a European Journal of Chemical Biology·Daniel FrancisJason Micklefield
Jan 20, 2017·Therapeutic Advances in Psychopharmacology·Ananya Mahapatra, Rishi Gupta
Jul 15, 2017·Journal of the American Chemical Society·David K RomneyFrances H Arnold
Aug 2, 2017·Angewandte Chemie·Janis FrickeDirk Hoffmeister
Oct 5, 2018·Evolution Letters·Hannah T ReynoldsJason C Slot

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Citations

Mar 14, 2019·Chembiochem : a European Journal of Chemical Biology·Allwin D McDonaldAndrew R Buller
Feb 27, 2020·Chemistry : a European Journal·Janis FrickeDirk Hoffmeister
Aug 12, 2018·Chembiochem : a European Journal of Chemical Biology·Felix BleiDirk Hoffmeister
Jun 1, 2019·Chembiochem : a European Journal of Chemical Biology·Janis FrickeDirk Hoffmeister
Jan 5, 2019·Organic & Biomolecular Chemistry·Hsiao-Ching LinYit-Heng Chooi
Dec 6, 2019·Chembiochem : a European Journal of Chemical Biology·Richard DemmlerDirk Hoffmeister
Oct 30, 2020·Drug Testing and Analysis·Klára GotvaldováMartin Kuchař
Nov 26, 2020·ChemPlusChem·Claudius LenzDirk Hoffmeister
Jan 7, 2021·Natural Product Reports·Markus GresslerDirk Hoffmeister
Jan 2, 2021·Forensic Science International : Synergy·Nicole S Jones, Jeffrey H Comparin
Jul 18, 2020·Chembiochem : a European Journal of Chemical Biology·Ella Watkins-DulaneyFrances Arnold
Mar 6, 2021·Journal of Natural Products·Janis FrickeDirk Hoffmeister
Jul 31, 2021·F1000Research·Kevin McKernanStephen McLaughlin
Jun 2, 2021·Chemistry : a European Journal·Claudius LenzDirk Hoffmeister

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