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Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor-Induced Combinatorial Pairing of Stig Cyclases.
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.
Afiliación
  • Li S; Life Sciences Institute, Department of Medicinal Chemistry, The University of Michigan, USA.
  • Newmister SA; Life Science Institute, The University of Michigan, USA.
  • Lowell AN; Life Science Institute, The University of Michigan, USA.
  • Zi J; Department of Chemistry, Virginia Tech, Blacksburg, VA, 24061, USA.
  • Chappell CR; Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, 60612, USA.
  • Yu F; Department of Molecular, Cellular & Developmental Biology, The University of Michigan, USA.
  • Hohlman RM; Life Science Institute, The University of Michigan, USA.
  • Orjala J; Life Sciences Institute, Department of Medicinal Chemistry, The University of Michigan, USA.
  • Williams RM; Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, 60612, USA.
  • Sherman DH; Department of Chemistry, Colorado State University, Fort Collins, CO, 80523, USA.
Angew Chem Int Ed Engl ; 59(21): 8166-8172, 2020 05 18.
Article en En | MEDLINE | ID: mdl-32052896
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.
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Proteínas Bacterianas / Alcaloides Indólicos / Indoles / Liasas Idioma: En Revista: Angew Chem Int Ed Engl Año: 2020 Tipo del documento: Article País de afiliación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Proteínas Bacterianas / Alcaloides Indólicos / Indoles / Liasas Idioma: En Revista: Angew Chem Int Ed Engl Año: 2020 Tipo del documento: Article País de afiliación: Estados Unidos