Albert Hofmann isolated and determined the structure of psilocybin, the main ingredient in mushrooms that leads to the psychedelic effects, nearly 60 years ago. That discovery and subsequent mind-altering experiments by Harvard University psychologist Timothy F. Leary have left scientists longing to develop a large-scale synthesis of the compound for medical uses, which include treating anxiety and depression in terminal cancer patients and treating nicotine addiction. Yet no one has been able to unravel the enzymatic pathway the mushrooms use to make psilocybin, until now.
Janis Fricke, Felix Blei, and Dirk Hoffmeister of Friedrich Schiller University Jena have identified and characterized to the greatest extent so far the four enzymes that the mushrooms use to make psilocybin. The team then developed the first enzymatic synthesis of the compound, setting the stage for its possible commercial production (Angew. Chem. Int. Ed. 2017, DOI: 10.1002/anie.201705489).
Psilocybin is the psychotropic tryptamine-derived natural product of Psilocybe carpophores, the so-called "magic mushrooms". Although its structure has been known for 60 years, the enzymatic basis of its biosynthesis has remained obscure. We characterized four psilocybin biosynthesis enzymes. These include i) PsiD which represents a new class of fungal l-tryptophan decarboxylases, ii) PsiK, that catalyzes the phosphotransfer step, iii) the methyl transferase PsiM, catalyzing iterative N-methyltransfer as terminal biosynthetic step, and iv) PsiH, a monooxygenase. In a combined PsiD/PsiK/PsiM reaction, psilocybin was synthesized enzymatically in a step-economic route from 4-hydroxy-l-tryptophan. Given the renewed pharmaceutical interest in psilocybin, our results may lay the foundation for its biotechnological production.
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