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The majority of\n                    <jats:bold>1<\/jats:bold>\n                    \u2010producing species belongs to the eponymous genus\n                    <jats:italic>Psilocybe<\/jats:italic>\n                    , for which the biosynthetic events, beginning from\n                    <jats:sc>l<\/jats:sc>\n                    \u2010tryptophan (\n                    <jats:bold>2<\/jats:bold>\n                    ), and the involved enzymes have thoroughly been characterized. Some\n                    <jats:italic>Inocybe<\/jats:italic>\n                    (fiber cap) species, among them\n                    <jats:italic>Inocybe corydalina<\/jats:italic>\n                    , produce\n                    <jats:bold>1<\/jats:bold>\n                    as well. In product formation assays, we characterized four recombinantly produced biosynthesis enzymes of this species in vitro: IpsD, a pyridoxal\u20105\u2032\u2010phosphate\u2010dependent\n                    <jats:sc>l<\/jats:sc>\n                    \u2010tryptophan decarboxylase, the kinase IpsK, and two near\u2010identical methyltransferases, IpsM1 and IpsM2. The fifth enzyme, the insoluble monooxygenase IpsH, was analyzed in silico. Surprisingly, none of the reactions intrinsic to the\n                    <jats:bold>1<\/jats:bold>\n                    pathway in\n                    <jats:italic>Psilocybe<\/jats:italic>\n                    species takes place in\n                    <jats:italic>I. corydalina<\/jats:italic>\n                    . Contrasting the situation in\n                    <jats:italic>Psilocybe<\/jats:italic>\n                    , the\n                    <jats:italic>Inocybe<\/jats:italic>\n                    pathway is branched and leads to baeocystin (4\u2010phosphoryloxy\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methyltryptamine,\n                    <jats:bold>3<\/jats:bold>\n                    ) as a second end product. Our results demonstrate that mushrooms recruited distantly or entirely unrelated enzymes to evolve the metabolic capacity for\n                    <jats:bold>1<\/jats:bold>\n                    biosynthesis twice independently.\n                  <\/jats:p>","DOI":"10.1002\/anie.202512017","type":"journal-article","created":{"date-parts":[[2025,9,22]],"date-time":"2025-09-22T06:26:54Z","timestamp":1758522414000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Dissimilar Reactions and Enzymes for Psilocybin Biosynthesis in\n                    <i>Inocybe<\/i>\n                    and\n                    <i>Psilocybe<\/i>\n                    Mushrooms"],"prefix":"10.1002","volume":"64","author":[{"given":"Tim","family":"Sch\u00e4fer","sequence":"first","affiliation":[{"name":"Pharmaceutical Microbiology Friedrich Schiller University  Winzerlaer Str. 2 07745 Jena Germany"},{"name":"Pharmaceutical Microbiology Leibniz Institute for Natural Product Research and Infection Biology \u2013 Hans\u2010Kn\u00f6ll\u2010Institute  Beutenbergstrasse 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fabian","family":"Haun","sequence":"additional","affiliation":[{"name":"Pharmaceutical Microbiology Friedrich Schiller University  Winzerlaer Str. 2 07745 Jena Germany"},{"name":"Pharmaceutical Microbiology Leibniz Institute for Natural Product Research and Infection Biology \u2013 Hans\u2010Kn\u00f6ll\u2010Institute  Beutenbergstrasse 11a 07745 Jena Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3300-6965","authenticated-orcid":false,"given":"Bernhard","family":"Rupp","sequence":"additional","affiliation":[{"name":"Department of General, Inorganic and Theoretical Chemistry University of Innsbruck  Innrain 82 6020 Innsbruck Austria"},{"name":"k.k. 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