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- Title
Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor‐Induced Combinatorial Pairing of Stig Cyclases.
- Authors
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.
- 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.
- Subjects
CYCLASES; ELECTROPHILIC substitution reactions; METABOLITES; STEREOSELECTIVE reactions; NATURAL products
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 21, p8243
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.201913686