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In this work, we report that a gene encoding cytochrome P450 monooxygenase CYP76M57, which we name AMI synthase (AMIS), enables the production of gramine in\n            <jats:italic>Nicotiana benthamiana<\/jats:italic>\n            ,\n            <jats:italic>Arabidopsis thaliana<\/jats:italic>\n            , and\n            <jats:italic>Saccharomyces cerevisiae<\/jats:italic>\n            . We reconstituted gramine production in the gramine-free barley (\n            <jats:italic>Hordeum vulgare<\/jats:italic>\n            ) variety Golden Promise and eliminated it from cultivar Tafeno by Cas-mediated gene editing. In vitro experiments unraveled that an unexpected cryptic oxidative rearrangement underlies this noncanonical conversion of an amino acid to a chain-shortened biogenic amine. The discovery of the genetic basis of gramine formation now permits tailor-made optimization of gramine-linked traits in barley by plant breeding.\n          <\/jats:p>","DOI":"10.1126\/science.adk6112","type":"journal-article","created":{"date-parts":[[2024,3,28]],"date-time":"2024-03-28T17:59:47Z","timestamp":1711648787000},"page":"1448-1454","update-policy":"https:\/\/doi.org\/10.34133\/aaas_crossmark","source":"Crossref","is-referenced-by-count":35,"title":["Biosynthesis of the allelopathic alkaloid gramine in barley by a cryptic oxidative rearrangement"],"prefix":"10.1126","volume":"383","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3667-3640","authenticated-orcid":true,"given":"Sara Leite","family":"Dias","sequence":"first","affiliation":[{"name":"Department of Molecular Genetics, Leibniz Institute of Plant Genetics and Crop Plant Research (IPK), Corrensstr. 3, 06466 Seeland OT Gatersleben, 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