The structure of SpnF, a standalone enzyme that catalyzes [4 + 2] cycloaddition

被引:0
|
作者
Fage C.D. [1 ]
Isiorho E.A. [1 ]
Liu Y. [2 ]
Wagner D.T. [1 ]
Liu H.-W. [2 ,3 ]
Keatinge-Clay A.T. [1 ,3 ]
机构
[1] Department of Molecular Biosciences, University of Texas at Austin, Austin, TX
[2] Division of Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX
[3] Department of Chemistry, University of Texas at Austin, Austin, TX
基金
美国国家卫生研究院;
关键词
D O I
10.1038/nchembio.1768
中图分类号
学科分类号
摘要
In the biosynthetic pathway of the spinosyn insecticides, the tailoring enzyme SpnF performs a [4 + 2] cycloaddition on a 22-membered macrolactone to forge an embedded cyclohexene ring. To learn more about this reaction, which could potentially proceed through a Diels-Alder mechanism, we determined the 1.50-Å-resolution crystal structure of SpnF bound to S-adenosylhomocysteine. This sets the stage for advanced experimental and computational studies to determine the precise mechanism of SpnF-mediated cyclization. © 2015 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:256 / 258
页数:2
相关论文
共 50 条
  • [41] A novel enzyme that catalyzes the esterification of N-acetylsphingosine - Metabolism of C-2-ceramides
    Abe, A
    Shayman, JA
    Radin, NS
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (24) : 14383 - 14389
  • [42] One-step customized enzyme treatment catalyzes fiber dissociation and application based on structure of Wikstroemia bark
    Chen, Jian
    Wang, Bin
    Duan, Chengliang
    Huang, Xinkang
    Kui, Minghong
    Li, Jinpeng
    Xu, Jun
    Zeng, Jinsong
    Cao, Daxian
    Gao, Wenhua
    Wang, Yonghua
    Chen, Kefu
    CHEMICAL ENGINEERING JOURNAL, 2025, 503
  • [43] Crystal structure of LepI, a multifunctional SAM-dependent enzyme which catalyzes pericyclic reactions in leporin biosynthesis
    Chang, Zhenying
    Ansbacher, Tamar
    Zhang, Lilan
    Yang, Yong
    Ko, Tzu-Ping
    Zhang, Guimin
    Liu, Weidong
    Huang, Jian-Wen
    Dai, Longhai
    Guo, Rey-Ting
    Major, Dan Thomas
    Chen, Chun-Chi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (08) : 2070 - 2076
  • [44] [4+2]-CYCLOADDITION AND [2+4]-CYCLOADDITION PROCESSES OF 4,5-DICYANOPYRIDAZINE WITH 2,3-DIMETHYLBUTA-1,3-DIENE
    NESI, R
    GIOMI, D
    TURCHI, S
    PAOLI, P
    TETRAHEDRON, 1994, 50 (30) : 9189 - 9194
  • [45] Chemoenzymatic Synthesis of Thiazolyl Peptide Natural Products Featuring an Enzyme-Catalyzed Formal [4+2] Cycloaddition
    Wever, Walter J.
    Bogart, Jonathan W.
    Baccile, Joshua A.
    Chan, Andrew N.
    Schroeder, Frank C.
    Bowers, Albert A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (10) : 3494 - 3497
  • [46] Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity
    He, Wenni
    Liu, Miaomiao
    Li, Xiaolin
    Zhang, Xiaoping
    Abdel-Mageed, Wael M.
    Li, Li
    Wang, Wenzhao
    Zhang, Jingyu
    Han, Jianying
    Dai, Huanqin
    Quinn, Ronald J.
    Liu, Hung-wen
    Luo, Houwei
    Zhang, Lixin
    Liu, Xueting
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2016, 100 (19) : 8349 - 8357
  • [47] Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity
    Wenni He
    Miaomiao Liu
    Xiaolin Li
    Xiaoping Zhang
    Wael M. Abdel-Mageed
    Li Li
    Wenzhao Wang
    Jingyu Zhang
    Jianying Han
    Huanqin Dai
    Ronald J. Quinn
    Hung-wen Liu
    Houwei Luo
    Lixin Zhang
    Xueting Liu
    Applied Microbiology and Biotechnology, 2016, 100 : 8349 - 8357
  • [48] Award Address (Arthur C. Cope Late Career Scholars Award sponsored by the Arthur C. Cope Fund). Mechanistic studies of SpnF-catalyzed [4+2] cycloaddition in spinosyn A biosynthesis
    Liu, Hung-Wen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [49] Application of [4+2] Cycloaddition Reaction of Tetrazine with Cyclooctyne in the Construction of Pyridazine Structure with Axial Chirality
    Cai, Zhengjun
    Gao, Jianbao
    Li, Bai
    Zhong, Yuan
    Feng, Xing
    Xue, Jijun
    Jiang, Xianxing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (05) : 1138 - 1146
  • [50] 3,5-Diphenyl-2-phosphafuran: Synthesis, Structure, and Thermally Reversible [4+2] Cycloaddition Chemistry
    Riu, Martin-Louis Y.
    Cummins, Christopher C.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (22): : 14810 - 14816