{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1360565166754839040.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1038/nchembio.1366"}},{"identifier":{"@type":"URI","@value":"http://www.nature.com/articles/nchembio.1366.pdf"}},{"identifier":{"@type":"URI","@value":"http://www.nature.com/articles/nchembio.1366"}},{"identifier":{"@type":"PMID","@value":"24121553"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk"}],"description":[{"notation":[{"@value":"Spirotryprostatins, an indole alkaloid class of nonribosomal peptides isolated from Aspergillus fumigatus, are known for their antimitotic activity in tumor cells. Because spirotryprostatins and many other chemically complex spiro-carbon-bearing natural products exhibit useful biological activities, identifying and understanding the mechanism of spiro-carbon biosynthesis is of great interest. Here we report a detailed study of spiro-ring formation in spirotryprostatins from tryprostatins derived from the fumitremorgin biosynthetic pathway, using reactants and products prepared with engineered yeast and fungal strains. Unexpectedly, FqzB, an FAD-dependent monooxygenase from the unrelated fumiquinazoline biosynthetic pathway, catalyzed spiro-carbon formation in spirotryprostatin A via an epoxidation route. Furthermore, FtmG, a cytochrome P450 from the fumitremorgin biosynthetic pathway, was determined to catalyze the spiro-ring formation in spirotryprostatin B. Our results highlight the versatile role of oxygenating enzymes in the biosynthesis of structurally complex natural products and indicate that cross-talk of different biosynthetic pathways allows product diversification in natural product biosynthesis."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380847869920759044","@type":"Researcher","foaf:name":[{"@value":"Yuta Tsunematsu"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920759040","@type":"Researcher","foaf:name":[{"@value":"Noriyasu Ishikawa"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920759043","@type":"Researcher","foaf:name":[{"@value":"Daigo Wakana"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920759042","@type":"Researcher","foaf:name":[{"@value":"Yukihiro Goda"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920759045","@type":"Researcher","foaf:name":[{"@value":"Hiroshi Noguchi"}]},{"@id":"https://cir.nii.ac.jp/crid/1420564276176313856","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"60500808"},{"@type":"NRID","@value":"1000060500808"},{"@type":"NRID","@value":"9000397945808"},{"@type":"NRID","@value":"9000410192624"},{"@type":"NRID","@value":"9000410999883"},{"@type":"NRID","@value":"9000006167501"},{"@type":"NRID","@value":"9000403270298"},{"@type":"NRID","@value":"9000410192620"},{"@type":"NRID","@value":"9000414109891"},{"@type":"NRID","@value":"9000412364273"},{"@type":"NRID","@value":"9000409467977"},{"@type":"NRID","@value":"9000258718723"},{"@type":"NRID","@value":"9000411077227"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/hisaom"}],"foaf:name":[{"@value":"Hisao Moriya"}]},{"@id":"https://cir.nii.ac.jp/crid/1380565166754839040","@type":"Researcher","foaf:name":[{"@value":"Kinya Hotta"}]},{"@id":"https://cir.nii.ac.jp/crid/1420001326221550208","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"50360938"},{"@type":"NRID","@value":"1000050360938"},{"@type":"NRID","@value":"9000006766176"},{"@type":"NRID","@value":"9000401962405"},{"@type":"NRID","@value":"9000257965586"},{"@type":"NRID","@value":"9000406289041"},{"@type":"NRID","@value":"9000410874499"},{"@type":"NRID","@value":"9000257965490"},{"@type":"NRID","@value":"9000382231161"},{"@type":"NRID","@value":"9000401545679"},{"@type":"NRID","@value":"9000412382349"},{"@type":"NRID","@value":"9000291273678"},{"@type":"NRID","@value":"9000273020065"},{"@type":"NRID","@value":"9000414102144"},{"@type":"NRID","@value":"9000311788766"},{"@type":"NRID","@value":"9000281375328"},{"@type":"NRID","@value":"9000253179401"},{"@type":"NRID","@value":"9000363283571"},{"@type":"NRID","@value":"9000019195547"},{"@type":"NRID","@value":"9000409026226"},{"@type":"NRID","@value":"9000018471704"},{"@type":"NRID","@value":"9000257965482"},{"@type":"NRID","@value":"9000019145232"},{"@type":"NRID","@value":"9000410922769"},{"@type":"NRID","@value":"9000019239598"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/kenjiw"}],"foaf:name":[{"@value":"Kenji Watanabe"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"15524450"},{"@type":"EISSN","@value":"15524469"}],"prism:publicationName":[{"@value":"Nature Chemical Biology"}],"dc:publisher":[{"@value":"Springer Science and Business Media LLC"}],"prism:publicationDate":"2013-10-13","prism:volume":"9","prism:number":"12","prism:startingPage":"818","prism:endingPage":"825"},"reviewed":"false","dc:rights":["http://www.springer.com/tdm"],"url":[{"@id":"http://www.nature.com/articles/nchembio.1366.pdf"},{"@id":"http://www.nature.com/articles/nchembio.1366"}],"createdAt":"2013-10-13","modifiedAt":"2023-05-18","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Models,%20Molecular","dc:title":"Models, Molecular"},{"@id":"https://cir.nii.ac.jp/all?q=Molecular%20Structure","dc:title":"Molecular Structure"},{"@id":"https://cir.nii.ac.jp/all?q=Aspergillus%20fumigatus","dc:title":"Aspergillus fumigatus"},{"@id":"https://cir.nii.ac.jp/all?q=Blotting,%20Western","dc:title":"Blotting, Western"},{"@id":"https://cir.nii.ac.jp/all?q=Antineoplastic%20Agents","dc:title":"Antineoplastic Agents"},{"@id":"https://cir.nii.ac.jp/all?q=Saccharomyces%20cerevisiae","dc:title":"Saccharomyces cerevisiae"},{"@id":"https://cir.nii.ac.jp/all?q=Piperazines","dc:title":"Piperazines"},{"@id":"https://cir.nii.ac.jp/all?q=Structure-Activity%20Relationship","dc:title":"Structure-Activity Relationship"},{"@id":"https://cir.nii.ac.jp/all?q=Gene%20Expression%20Regulation,%20Fungal","dc:title":"Gene Expression Regulation, Fungal"},{"@id":"https://cir.nii.ac.jp/all?q=Spiro%20Compounds","dc:title":"Spiro Compounds"},{"@id":"https://cir.nii.ac.jp/all?q=DNA,%20Fungal","dc:title":"DNA, 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