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Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases
dc.contributor.authorLi, Shasha
dc.contributor.authorNewmister, Sean A.
dc.contributor.authorLowell, Andrew N.
dc.contributor.authorZi, Jiachen
dc.contributor.authorChappell, Callie R.
dc.contributor.authorYu, Fengan
dc.contributor.authorHohlman, Robert M.
dc.contributor.authorOrjala, Jimmy
dc.contributor.authorWilliams, Robert M.
dc.contributor.authorSherman, David H.
dc.date.accessioned2020-06-03T15:23:20Z
dc.date.availableWITHHELD_12_MONTHS
dc.date.available2020-06-03T15:23:20Z
dc.date.issued2020-05-18
dc.identifier.citationLi, Shasha; Newmister, Sean A.; Lowell, Andrew N.; Zi, Jiachen; Chappell, Callie R.; Yu, Fengan; Hohlman, Robert M.; Orjala, Jimmy; Williams, Robert M.; Sherman, David H. (2020). "Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases." Angewandte Chemie 132(21): 8243-8249.
dc.identifier.issn0044-8249
dc.identifier.issn1521-3757
dc.identifier.urihttps://hdl.handle.net/2027.42/155506
dc.description.abstractStereospecific polycyclic core formation of hapalindoles and fischerindoles is controlled by Stig cyclases through a three‐step cascade involving Cope rearrangement, 6‐exo‐trig cyclization, and a final electrophilic aromatic substitution. Reported here is a comprehensive study of all currently annotated Stig cyclases, revealing that these proteins can assemble into heteromeric complexes, induced by Ca2+, to cooperatively control the stereochemistry of hapalindole natural products.Die stereospezifische Bildung des polycyclischen Kerns der Hapalindole und Fischerindole wird durch Stig‐Cyclasen gesteuert, die eine dreistufige Kaskade aus Cope‐Umlagerung, 6‐exo‐trig‐Cyclisierung und elektrophiler aromatischer Substitution vermitteln. Die Proteine können sich induziert durch Ca2+ zu heterotrimeren Komplexen zusammenlagern, um auf kooperative Weise die Stereochemie zu steuern.
dc.publisherWiley Periodicals, Inc.
dc.publisherAcademic Press
dc.subject.otherOligomerisierung
dc.subject.otherUmlagerungen
dc.subject.otherBiokatalyse
dc.subject.otherCyclasen
dc.subject.otherIndole
dc.titleControl of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/155506/1/ange201913686.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/155506/2/ange201913686-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/155506/3/ange201913686_am.pdf
dc.identifier.doi10.1002/ange.201913686
dc.identifier.sourceAngewandte Chemie
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