调控不同哈巴因类代谢物的立体选择性是由辅因子诱导的柱晶烷环化酶组合配对介导的。
Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor-Induced Combinatorial Pairing of Stig Cyclases.
机构信息
Life Sciences Institute, Department of Medicinal Chemistry, The University of Michigan, USA.
Life Science Institute, The University of Michigan, USA.
出版信息
Angew Chem Int Ed Engl. 2020 May 18;59(21):8166-8172. doi: 10.1002/anie.201913686. Epub 2020 Mar 19.
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 Ca , to cooperatively control the stereochemistry of hapalindole natural products.
摘要
通过涉及 Cope 重排、6-endo-trig 环化和最终亲电芳香取代的三步级联反应，Stig 环化酶控制了 hapalindoles 和 fischerindoles 的立体特异性多环核心形成。本文全面研究了所有现有注释的 Stig 环化酶，揭示了这些蛋白可以组装成异源复合物，由 Ca 诱导，协同控制 hapalindole 天然产物的立体化学。
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