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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.accessioned2020-07-02T20:32:35Z
dc.date.availableWITHHELD_11_MONTHS
dc.date.available2020-07-02T20:32:35Z
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 International Edition 59(21): 8166-8172.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/155895
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.Assembly control: Stereospecific formation of the polycyclic core 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. The proteins can assemble into heteromeric complexes, induced by Ca2+, to cooperatively control the stereochemistry of hapalindole natural products.
dc.publisherWiley Periodicals, Inc.
dc.publisherAcademic Press
dc.subject.otherbiocatalysis
dc.subject.othercyclases
dc.subject.otherindoles
dc.subject.otheroligomerization
dc.subject.otherrearrangements
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.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/155895/1/anie201913686-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/155895/2/anie201913686_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/155895/3/anie201913686.pdf
dc.identifier.doi10.1002/anie.201913686
dc.identifier.sourceAngewandte Chemie International Edition
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