Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.

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Tytuł:: Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.
Autorzy:: Fujiyama K; Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho, Minami, Tottori, 680-8552, Japan.; Current address: Dormancy and Adaptation Research Unit, RIKEN Center for Sustainable Resource Science, 1-7-22 Suehiro, Tsurumi, Yokohama, Kanagawa, 230-0045, Japan.
Kato N; Natural Product Biosynthesis Research Unit, RIKEN Center for Sustainable Research Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.; Faculty of Agriculture, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka, 573-0101, Japan.
Re S; Laboratory for Biomolecular Function Simulation, RIKEN Center for Biosystems Dynamics Research, 2-2-3 Minatojima-minami-machi, Chuo-ku, Kobe, Hyogo, 650-0047, Japan.; Artificial Intelligence Center for Health and Biomedical Research, National Institutes of Biomedical Innovation, Health, and Nutrition, 7-6-8, Saito-Asagi, Ibaraki, Osaka, 567-0085, Japan.
Kinugasa K; Natural Product Biosynthesis Research Unit, RIKEN Center for Sustainable Research Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
Watanabe K; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
Takita R; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
Nogawa T; Chemical Biology Research Group, RIKEN Center for Sustainable Research Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
Hino T; Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho, Minami, Tottori, 680-8552, Japan.; Center for Research on Green Sustainable Chemistry, Tottori University, 4-101 Koyama-cho, Minami, Tottori, 680-8552, Japan.
Osada H; Chemical Biology Research Group, RIKEN Center for Sustainable Research Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
Sugita Y; Laboratory for Biomolecular Function Simulation, RIKEN Center for Biosystems Dynamics Research, 2-2-3 Minatojima-minami-machi, Chuo-ku, Kobe, Hyogo, 650-0047, Japan.; Theoretical Molecular Science Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.; Computational Biophysics Research Team, RIKEN Center for Computational Science, 7-1-26 Minatojima-minami-machi, Chuo-ku, Kobe, Hyogo, 650-0047, Japan.
Takahashi S; Natural Product Biosynthesis Research Unit, RIKEN Center for Sustainable Research Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
Nagano S; Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-cho, Minami, Tottori, 680-8552, Japan.; Center for Research on Green Sustainable Chemistry, Tottori University, 4-101 Koyama-cho, Minami, Tottori, 680-8552, Japan.
Źródło:: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Oct 04; Vol. 60 (41), pp. 22401-22410. Date of Electronic Publication: 2021 Jul 05.
Typ publikacji:: Journal Article; Research Support, Non-U.S. Gov't
Język:: English
Imprint Name(s):: Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
MeSH Terms:: Naphthalenes/*metabolism
Pyrrolidinones/*metabolism
Tetrahydronaphthalenes/*metabolism
Models, Molecular ; Molecular Conformation ; Naphthalenes/chemistry ; Stereoisomerism
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Contributed Indexing:: Keywords: [4+2] cycloaddition; biosynthesis; molecular dynamics; natural products; stereoselectivity
Substance Nomenclature:: 0 (Naphthalenes)
0 (Pyrrolidinones)
0 (Tetrahydronaphthalenes)
57749-43-6 (equisetin)
88451Q4XYF (decalin)
Entry Date(s):: Date Created: 20210614 Date Completed: 20211116 Latest Revision: 20231107
Update Code:: 20240105
PubMed Central ID:: PMC8518865
DOI:: 10.1002/anie.202106186
PMID:: 34121297
: Czasopismo naukowe

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Enzymes catalyzing [4+2] cycloaddition have attracted increasing attention because of their key roles in natural product biosynthesis. Here, we solved the X-ray crystal structures of a pair of decalin synthases, Fsa2 and Phm7, that catalyze intramolecular [4+2] cycloadditions to form enantiomeric decalin scaffolds during biosynthesis of the HIV-1 integrase inhibitor equisetin and its stereochemical opposite, phomasetin. Computational modeling, using molecular dynamics simulations as well as quantum chemical calculations, demonstrates that the reactions proceed through synergetic conformational constraints assuring transition state-like substrates folds and their stabilization by specific protein-substrate interactions. Site-directed mutagenesis experiments verified the binding models. Intriguingly, the flexibility of bound substrates is largely different in two enzymes, suggesting the distinctive mechanism of dynamics regulation behind these stereoselective reactions. The proposed reaction mechanism herein deepens the basic understanding how these enzymes work but also provides a guiding principle to create artificial enzymes.
(© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)

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