- Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase-Enhanced Reactions
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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.
- Blei, Felix,Baldeweg, Florian,Fricke, Janis,Hoffmeister, Dirk
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p. 10028 - 10031
(2018/07/29)
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- Chemo-enzymatic synthesis and characterization of L-tryptophans selectively 13C-enriched or hydroxylated in the six-membered ring using transformed Escherichia coli cells
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L-(3a-13C)- and L-(6-13C)tryptophan have been synthesized from simple labelled compounds via a single reaction scheme based on the conversion of 1,3-cyclohexanedione into indole.The labelled indoles have been converted in one step into the corresponding L-tryptophans using transformed Escherichia coli cells with large amounts of the enzyme, tryptophan synthease.The same reaction scheme has been used for the synthesis of 4- and 7-indolol.These hydroxyindoles together with 5-indolol have been converted into 4-, 7- and 5-hydroxy-L-tryptophan, respectively, using theEscherichia coli cells.The latter compound is the immediate precursor of the neurotransmitter, serotonin.It appears that 7-indolol is the only indole derivative which is converted faster than unsubstituted indole by the enzyme, tryptophan synthease.With the preparation of L-(3a-13C)- and L-(6-13C)tryptophan, we have completed the series of indoles and L-tryptophans with a stable isotope (13C, 15N or 2H) in the aromatic ring.In this paper, we also discuss the NMR parameters of these mono-isotopically labelled systems.
- Berg, E. M. M. van den,Jansen, F. J. H. M.,Goede, A. T. J. W. de,Baldew, A. U.,Lugtenburg, J.
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p. 287 - 297
(2007/10/02)
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