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In seed plants, the initial step of cyanogenic glycoside biosynthesis\u2014the conversion of an amino acid to the corresponding aldoxime\u2014is catalyzed by a cytochrome P450 from the CYP79 family. An evolutionary conundrum arises, as no CYP79s have been identified in ferns, despite cyanogenic glycoside occurrence in several fern species. Here, we report that a flavin-dependent monooxygenase (fern oxime synthase; FOS1), catalyzes the first step of cyanogenic glycoside biosynthesis in two fern species (\n                    <jats:italic>Phlebodium aureum<\/jats:italic>\n                    and\n                    <jats:italic>Pteridium aquilinum<\/jats:italic>\n                    ), demonstrating convergent evolution of biosynthesis across the plant kingdom. The FOS1 sequence from the two species is near identical (98%), despite diversifying 140 MYA. Recombinant FOS1 was isolated as a catalytic active dimer, and in planta, catalyzes formation of an N-hydroxylated primary amino acid; a class of metabolite not previously observed in plants.\n                  <\/jats:p>","DOI":"10.1038\/s42003-020-01224-5","type":"journal-article","created":{"date-parts":[[2020,9,11]],"date-time":"2020-09-11T06:09:52Z","timestamp":1599804592000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":49,"title":["A flavin-dependent monooxygenase catalyzes the initial step in cyanogenic glycoside synthesis in ferns"],"prefix":"10.1038","volume":"3","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9332-6071","authenticated-orcid":false,"given":"Sara","family":"Thodberg","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9787-8386","authenticated-orcid":false,"given":"Mette","family":"S\u00f8rensen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1392-5091","authenticated-orcid":false,"given":"Matteo","family":"Bellucci","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2754-3518","authenticated-orcid":false,"given":"Christoph","family":"Crocoll","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3996-6529","authenticated-orcid":false,"given":"Amalie Kofoed","family":"Bendtsen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0583-5421","authenticated-orcid":false,"given":"David Ralph","family":"Nelson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5582-9463","authenticated-orcid":false,"given":"Mohammed Saddik","family":"Motawia","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3252-3119","authenticated-orcid":false,"given":"Birger Lindberg","family":"M\u00f8ller","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elizabeth Heather Jakobsen","family":"Neilson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2020,9,11]]},"reference":[{"key":"1224_CR1","doi-asserted-by":"crossref","first-page":"1764","DOI":"10.1016\/S0031-9422(00)97475-2","volume":"15","author":"NL Harper","year":"1976","unstructured":"Harper, N. 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