@article{f78c55c0e0804826a72ffa1ddcf5c10f,
title = "Deciphering Pyrrolidine and Olefin Formation Mechanism in Kainic Acid Biosynthesis",
abstract = "Metalloenzyme-catalyzed cyclization involving C-H bond activation is a powerful strategy to construct molecular complexity found in natural product biosynthesis. In the isodomoic acid and kainic acid biosynthetic pathways, mononuclear non-heme iron enzymes catalyze cyclization along with desaturation reactions that install the pyrrolidine and the olefin. Using complementary approaches, a plausible reaction pathway of kainic acid formation is established. Following H atom abstraction by an Fe(IV)-oxo species, the resulting radical interacts with the N-prenyl group to promote pyrrolidine installation. The reaction then undergoes a carbocation-triggered desaturation to construct kainic acid.",
keywords = "C-H activation, cyclization, desaturation, enzyme mechanism, metalloenzyme",
author = "Chen, {Tzu Yu} and Shan Xue and Tsai, {Wei Chih} and Chien, {Tun Cheng} and Yisong Guo and Chang, {Wei Chen}",
note = "Funding Information: This work was supported by North Carolina State University, Carnegie Mellon University, National Taiwan Normal University, and Research Grants MOST 109-2113-M-003-005 from Ministry of Science and Technology, Taiwan and Higher Education Sprout Project from Ministry of Education, Taiwan. We would like to thank Dr. Ji-Wang Chern (National Taiwan University) for the generous gift of kainic acid and Dr. Wei-Lung Wang (Department of Biology, National Changhua University of Education) for helpful discussion. Funding Information: This work was supported by North Carolina State University, Carnegie Mellon University, National Taiwan Normal University and Research Grants MOST 109-2113-M-003-005 from Ministry of Science and Technology, Taiwan and Higher Education Sprout Project from Ministry of Education, Taiwan. We would like to thank Dr. Ji-Wang Chern (National Taiwan University) for the generous gift of kainic acid and Dr. Wei-Lung Wang (Department of Biology, National Changhua University of Education) for helpful discussion. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",
year = "2021",
month = jan,
day = "1",
doi = "10.1021/acscatal.0c03879",
language = "English",
volume = "11",
pages = "278--282",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "1",
}