Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases
dc.contributor.author | Li, Shasha | |
dc.contributor.author | Newmister, Sean A. | |
dc.contributor.author | Lowell, Andrew N. | |
dc.contributor.author | Zi, Jiachen | |
dc.contributor.author | Chappell, Callie R. | |
dc.contributor.author | Yu, Fengan | |
dc.contributor.author | Hohlman, Robert M. | |
dc.contributor.author | Orjala, Jimmy | |
dc.contributor.author | Williams, Robert M. | |
dc.contributor.author | Sherman, David H. | |
dc.date.accessioned | 2020-06-03T15:23:20Z | |
dc.date.available | WITHHELD_12_MONTHS | |
dc.date.available | 2020-06-03T15:23:20Z | |
dc.date.issued | 2020-05-18 | |
dc.identifier.citation | Li, 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.issn | 0044-8249 | |
dc.identifier.issn | 1521-3757 | |
dc.identifier.uri | https://hdl.handle.net/2027.42/155506 | |
dc.description.abstract | Stereospecific 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.publisher | Wiley Periodicals, Inc. | |
dc.publisher | Academic Press | |
dc.subject.other | Oligomerisierung | |
dc.subject.other | Umlagerungen | |
dc.subject.other | Biokatalyse | |
dc.subject.other | Cyclasen | |
dc.subject.other | Indole | |
dc.title | Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases | |
dc.type | Article | |
dc.rights.robots | IndexNoFollow | |
dc.subject.hlbsecondlevel | Chemistry | |
dc.subject.hlbsecondlevel | Chemical Engineering | |
dc.subject.hlbsecondlevel | Materials Science and Engineering | |
dc.subject.hlbtoplevel | Engineering | |
dc.subject.hlbtoplevel | Science | |
dc.description.peerreviewed | Peer Reviewed | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/155506/1/ange201913686.pdf | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/155506/2/ange201913686-sup-0001-misc_information.pdf | |
dc.description.bitstreamurl | https://deepblue.lib.umich.edu/bitstream/2027.42/155506/3/ange201913686_am.pdf | |
dc.identifier.doi | 10.1002/ange.201913686 | |
dc.identifier.source | Angewandte Chemie | |
dc.identifier.citedreference | S. Mo, A. Krunic, G. Chlipala, J. Orjala, J. Nat. Prod. 2009, 72, 894 – 899. | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | R. E. Moore, C. Cheuk, G. M. L. Patterson, J. Am. Chem. Soc. 1984, 106, 6456 – 6457; | |
dc.identifier.citedreference | V. Bhat, A. Dave, J. A. MacKay, V. H. Rawal, in The Alkaloids: Chemistry and Biology, Vol. 73 (Ed.: K. Hans-Joachim ), Academic Press, San Diego, 2014, pp. 65 – 160. | |
dc.identifier.citedreference | U. M. Acuña, S. Mo, J. Zi, J. Orjala, E. J. C. De Blanco, Anticancer Res. 2018, 38, 3299 – 3307. | |
dc.identifier.citedreference | K. Walton, M. Gantar, P. Gibbs, M. Schmale, J. Berry, Toxins 2014, 6, 3568 – 3581. | |
dc.identifier.citedreference | E. Cagide, P. G. Becher, M. C. Louzao, B. Espiña, M. R. Vieytes, F. Jüttner, L. M. Botana, Chem. Res. Toxicol. 2014, 27, 1696 – 1706. | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | S. Li, A. N. Lowell, F. Yu, A. Raveh, S. A. Newmister, N. Bair, J. M. Schaub, R. M. Williams, D. H. Sherman, J. Am. Chem. Soc. 2015, 137, 15366 – 15369; | |
dc.identifier.citedreference | M. L. Hillwig, Q. Zhu, X. Liu, ACS Chem. Biol. 2014, 9, 372 – 377; | |
dc.identifier.citedreference | M. L. Micallef, D. Sharma, B. M. Bunn, L. Gerwick, R. Viswanathan, M. C. Moffitt, BMC Microbiol. 2014, 14, 213 – 230; | |
dc.identifier.citedreference | M. L. Hillwig, H. A. Fuhrman, K. Ittiamornkul, T. J. Sevco, D. H. Kwak, X. Liu, ChemBioChem 2014, 15, 665 – 669. | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | S. Li, A. N. Lowell, S. A. Newmister, F. Yu, R. M. Williams, D. H. Sherman, Nat. Chem. Biol. 2017, 13, 467 – 469; | |
dc.identifier.citedreference | Q. Zhu, X. Liu, Angew. Chem. Int. Ed. 2017, 56, 9062 – 9066; Angew. Chem. 2017, 129, 9190 – 9194. | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | S. A. Newmister, S. Li, M. Garcia-Borràs, J. N. Sanders, S. Yang, A. N. Lowell, F. Yu, J. L. Smith, R. M. Williams, K. N. Houk, D. H. Sherman, Nat. Chem. Biol. 2018, 14, 345 – 351; | |
dc.identifier.citedreference | C. C. Chen, X. Hu, X. Tang, Y. Yang, T. P. Ko, J. Gao, Y. Zheng, J. W. Huang, Z. Yu, L. Li, S. Han, N. Cai, Y. Zhang, W. Liu, R. T. Guo, Angew. Chem. Int. Ed. 2018, 57, 15060 – 15064; Angew. Chem. 2018, 130, 15280 – 15284; | |
dc.identifier.citedreference | X. Tang, J. Xue, Y. Yang, T.-P. Ko, C.-Y. Chen, L. Dai, R.-T. Guo, Y. Zhang, C.-C. Chen, RSC Adv. 2019, 9, 13182 – 13185. | |
dc.identifier.citedreference | A. Raveh, S. Carmeli, J. Nat. Prod. 2007, 70, 196 – 201. | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | T. A. Smitka, R. Bonjouklian, L. Doolin, N. D. Jones, J. B. Deeter, W. Y. Yoshida, M. R. Prinsep, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1992, 57, 857 – 861; | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | Z. Lu, M. Yang, P. Chen, X. Xiong, A. Li, Angew. Chem. Int. Ed. 2014, 53, 13840 – 13844; Angew. Chem. 2014, 126, 14060 – 14064; | |
dc.identifier.citedreference | D. Klein, D. Daloze, J. C. Braekman, L. Hoffmann, V. Demoulin, J. Nat. Prod. 1995, 58, 1781 – 1785; | |
dc.identifier.citedreference | T. J. Maimone, Y. Ishihara, P. S. Baran, Tetrahedron 2015, 71, 3652 – 3665. | |
dc.identifier.citedreference | D. H. Dethe, S. Das, V. B. Kumar, N. A. Mir, Chem. Eur. J. 2018, 24, 8980 – 8984. | |
dc.identifier.citedreference | ||
dc.identifier.citedreference | J. Vonck, D. J. Mills, Curr. Opin. Struct. Biol. 2017, 46, 48 – 54; | |
dc.identifier.citedreference | V. Villeret, B. Clantin, C. Tricot, C. Legrain, M. Roovers, V. Stalon, N. Glansdorff, J. Van Beeumen, Proc. Natl. Acad. Sci. USA 1998, 95, 2801 – 2806. | |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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