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Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)
dc.contributor.authorKagiyama, Ippei
dc.contributor.authorKato, Hikaru
dc.contributor.authorNehira, Tatsuo
dc.contributor.authorFrisvad, Jens C.
dc.contributor.authorSherman, David H.
dc.contributor.authorWilliams, Robert M.
dc.contributor.authorTsukamoto, Sachiko
dc.date.accessioned2017-06-16T20:13:26Z
dc.date.available2017-06-16T20:13:26Z
dc.date.issued2016-01-18
dc.identifier.citationKagiyama, Ippei; Kato, Hikaru; Nehira, Tatsuo; Frisvad, Jens C.; Sherman, David H.; Williams, Robert M.; Tsukamoto, Sachiko (2016). "Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)." Angewandte Chemie 128(3): 1140-1144.
dc.identifier.issn0044-8249
dc.identifier.issn1521-3757
dc.identifier.urihttps://hdl.handle.net/2027.42/137451
dc.description.abstractSeven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides C and D contain endoperoxide and methylsulfonyl units, respectively. This fungus produced indole alkaloids containing an anti‐bicyclo[2.2.2]diazaoctane core, whereas A. protuberus and A. amoenus produced congeners with a syn‐bicyclo[2.2.2]diazaoctane core. Plausible biosynthetic pathways to access these cores within the three species likely arise from an intramolecular hetero Diels–Alder reaction.Sieben neue prenylierte Indolalkaloide wurden aus A. taichungensis isoliert. Dieser Pilz erzeugt Alkaloide mit anti‐Bicyclo[2.2.2]diazaoctan‐Kern, während A. protuberus und A. amoenus syn‐Derivate herstellen. Die Strukturdiversität der von Tryptophan abgeleiteten Sekundärmetaboliten deutet auf stereochemisch und strukturell hoch entwickelte Synthesefunktionen für Sekundärmetaboliten in diesen orthologen Pilzen hin.
dc.publisherWiley Periodicals, Inc.
dc.subject.otherStrukturaufklärung
dc.subject.otherAlkaloide
dc.subject.otherBiosynthese
dc.subject.otherCycloadditionen
dc.subject.otherNaturstoffe
dc.titleTaichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137451/1/ange201509462.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137451/2/ange201509462-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137451/3/ange201509462_am.pdf
dc.identifier.doi10.1002/ange.201509462
dc.identifier.sourceAngewandte Chemie
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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