Seeing the cis-Dihydroxylating Intermediate: A Mononuclear Nonheme Iron-Peroxo Complex in cis-Dihydroxylation Reactions Modeling Rieske Dioxygenases

Zhu, Wenjuan; Kumar, Akhilesh; Xiong, Jin; Abernathy, Macon J.; Li, Xiao-Xi; Seo, Mi Sook; Lee, Yong-Min; Sarangi, Ritimukta; Guo, Yisong; Nam, Wonwoo

doi:10.1021/jacs.2c13551

Title: Seeing the cis-Dihydroxylating Intermediate: A Mononuclear Nonheme Iron-Peroxo Complex in cis-Dihydroxylation Reactions Modeling Rieske Dioxygenases

Journal Article · Thu Feb 16 00:00:00 EST 2023 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c13551· OSTI ID:1991528

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Ewha Womans Univ., Seoul (Korea, Republic of)
Carnegie Mellon Univ., Pittsburgh, PA (United States)
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)
Ewha Womans Univ., Seoul (Korea, Republic of); Shandong Univ., Qingdao, Shandong (China)
Ewha Womans Univ., Seoul (Korea, Republic of); Univ. of Jinan (China)

The nature of reactive intermediates and the mechanism of the cis-dihydroxylation of arenes and olefins by Rieske dioxygenases and synthetic nonheme iron catalysts have been the topic of intense research over the past several decades. In this study, we report that a spectroscopically well characterized mononuclear nonheme iron(III)-peroxo complex reacts with olefins and naphthalene derivatives, yielding iron(III) cycloadducts that are isolated and characterized structurally and spectroscopically. Further, kinetics and product analysis reveal that the nonheme iron(III)-peroxo complex is a nucleophile that reacts with olefins and naphthalenes to yield cis-diol products. The present study reports the first example of the cis-dihydroxylation of substrates by a nonheme iron(III)-peroxo complex that yields cis-diol products.

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Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Research Foundation of Korea (NRF); National Institute of General Medical Sciences (NIGMS); National Institutes of Health (NIH)

Grant/Contract Number:: AC02-76SF00515; NRF-2021R1A3B1076539; NRF-2020R1I1A1A01074630; P30GM133894; R01GM125924

OSTI ID:: 1991528

Journal Information:: Journal of the American Chemical Society, Vol. 145, Issue 8; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Title: Seeing the cis-Dihydroxylating Intermediate: A Mononuclear Nonheme Iron-Peroxo Complex in cis-Dihydroxylation Reactions Modeling Rieske Dioxygenases

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