Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins

Zhiwen Liu; Fanglong Zhao; Boyang Zhao; Jie Yang; Joseph Ferrara; Banumathi Sankaran; B. V. Venkataram Prasad; Biki Bapi Kundu; George N. Phillips; Yang Gao; Liya Hu; Tong Zhu; Xue Gao

doi:10.1038/s41467-021-24421-0

Nature Communications (Jul 2021)

Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins

Zhiwen Liu,
Fanglong Zhao,
Boyang Zhao,
Jie Yang,
Joseph Ferrara,
Banumathi Sankaran,
B. V. Venkataram Prasad,
Biki Bapi Kundu,
George N. Phillips,
Yang Gao,
Liya Hu,
Tong Zhu,
Xue Gao

Affiliations

Zhiwen Liu: Department of Chemical and Biomolecular Engineering, Rice University
Fanglong Zhao: Department of Chemical and Biomolecular Engineering, Rice University
Boyang Zhao: Department of Molecular Virology and Microbiology, Baylor College of Medicine
Jie Yang: Department of Chemical and Biomolecular Engineering, Rice University
Joseph Ferrara: Rigaku Americas Corporation
Banumathi Sankaran: Department of Molecular Biophysics and Integrated Bioimaging, Berkeley Center for Structural Biology, Lawrence Berkeley National Laboratory
B. V. Venkataram Prasad: Department of Molecular Virology and Microbiology, Baylor College of Medicine
Biki Bapi Kundu: PhD Program in Systems, Synthetic, and Physical Biology, Rice University
George N. Phillips: Department of Biosciences, Rice University
Yang Gao: Department of Biosciences, Rice University
Liya Hu: Verna and Marrs McLean Department of Biochemistry and Molecular Biology, Baylor College of Medicine
Tong Zhu: Shanghai Engineering Research Center of Molecular Therapeutics & New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University
Xue Gao: Department of Chemical and Biomolecular Engineering, Rice University

DOI: https://doi.org/10.1038/s41467-021-24421-0
Journal volume & issue: Vol. 12, no. 1
pp. 1 – 12

Abstract

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Prenylated indole alkaloids contain spirooxindole rings with a 3R or 3S carbon stereocenter, which determines their bioactivities, but the biocatalytic mechanism controlling the 3R- or 3S-spirooxindole formation was unclear. Here, the authors report the biochemical and structural characterization of the oxygenase/semipinacolase CtdE that catalyses the 3S-spirooxindole construction in the biosynthesis of 21R-citrinadin A.

Published in Nature Communications

ISSN: 2041-1723 (Online)
Publisher: Nature Portfolio
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://www.nature.com/ncomms/

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