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Nonheme Iron-Catalyzed Enantioselective cis-Dihydroxylation of Aliphatic Acrylates as Mimics of Rieske Dioxygenases

CCS Chemistry 2022年第7期4卷 2369-2381页

作者： Jie Chen Xiu Luo Ying Sun Si Si Yuankai Xu Yong-Min Lee wonwoo nam Bin Wang School of Chemistry and Chemical Engineering University of JinanJinan 250022 Department of Chemistry and Nano Science Ewha Womans UniversitySeoul 03760

Enantioselective cis-dihydroxylation of alkenes represents an ideal route to synthesize enantioenriched syn-2,3-dihydroxy esters that are important structural motifs in numerous biologically and pharmaceutically relevant molecules.Bioinspired nonheme iron-catalyzed enantioselective cis-dihydroxylation meets the requirement of the modern synthetic chemistry from the atomic economy,green chemistry,and sustainable development perspectives.However,nonheme iron-catalyzed enantioselective cis-dihydroxylation is much underdeveloped because of the formidable challenges of controlling chemo-and enantioselectivities and product selectivity caused by the competitive epoxidation,cis-dihydroxylation,and overoxidation reactions.Herein,we disclose the fabrication of a biologically inspired nonheme iron complex-catalyzed enantioselective cis-dihydroxylation of multisubstituted acrylates using hydrogen peroxide(H_(2)O_(2))as the terminal oxidant by controlling the non-ligating or weakly ligating counterions of iron(Ⅱ)complexes,demonstrating a dramatic counteranion effect on the enantioselective cisdihydroxylation of olefins by H_(2)O_(2) catalyzed by nonheme iron complexes.A range of structurally disparate alkenes were transformed to the corresponding syn-2,3-dihydroxy esters in practically useful yields with exquisite chemo-and enantioselectivities(up to 99% ee).Given the mild and benign nature of this biologically inspired oxidation system as well as the ubiquity and synthetic utility of enantioenriched syn-2,3-dihydroxy esters as pharmaceuticals candidates and natural products,we expect that this strategy could serve as a promising complement to the well-known Sharpless asymmetric dihydroxylation,which is the chemical reaction of an alkene with OsO_(4) to produce a vicinal diol.

关键词： bioinspired catalysis Rieske dioxygenase cis-dihydroxylation nonheme iron catalyst tetradentate nitrogen-donor ligand

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A cobalt(Ⅱ)porphyrin with a tethered imidazole for efficient oxygen reduction and evolution electrocatalysis

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Journal of Energy Chemistry 2023年第1期76卷 617-621,I0015页

作者： Xialiang Li Ping Li Jindou Yang Lisi Xie Ni Wang Haitao Lei Chaochao Zhang Wei Zhang Yong-Min Lee Weiqiang Zhang Shunichi Fukuzumi wonwoo nam Rui Cao Key Laboratory of Applied Surface and Colloid Chemistry Ministry of EducationSchool of Chemistry and Chemical EngineeringShaanxi Normal UniversityXi'an 710119 ShaanxiChina Department of Chemistry and Nano Science Ewha Womans UniversitySeoul 03760Republic of Korea

Electrocatalytic oxygen reduction and evolution reactions are involved in new energy conversion and storage technologies,such as various fuel cells and metal-air batteries and also water splitting devices[1,2].However... 详细信息

关键词： Molecular electrocatalysis Cobalt porphyrin Axial ligand effect Oxygen reduction reaction Oxygen evolution reaction

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Theoretical investigation on the elusive biomimetic iron(Ⅲ)-iodosylarene chemistry: An unusual hydride transfer triggers the Ritter reaction

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Chinese Chemical Letters 2021年第12期32卷 3857-3861页

作者： Lanping Gao Xiaolu Chen Dongru Sun Hua Zhao Yufen Zhao wonwoo nam Yong Wang Institute of Drug Discovery Technology Ningbo UniversityNingbo 315211China Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences Ningbo UniversityNingbo 3152UChina Department of Chemistry and Nano Science Ewha Womans UniversitySeoul 03760Korea

Introduction of iodosylarnes into biomimetic nonheme chemistry has made great achievement on identification of the subtle metal-oxygen reaction intermediates. However, after more than three decades of experimental and theoretical efforts the nature of the metal-iodosylarene adducts and the related dichotomous one-oxidant/multiple-oxident controversy have remained a matter of speculation. Herein, we report a theoretical study of the structure-activity relationship of the noted iron(Ⅲ)-iodsylarene complex,FeⅢ(Ph IO)(OTf)3(1), in oxygenation of cyclohexene. The calculated results revealed that 1 behaves like a chameleon by adapting its roles as a 2 e-oxidant or an oxygen donor, as a response to the regioselective attack of the C–H bond and the C=C bond. The oxidative C–H bond activation by 1 was found, for the first time, to proceed via a novel hydride transfer process to form a cyclohexene carbonium intermediate,such non-rebound step triggers the Ritter reaction to uptake an acetonitrile molecule to form the amide product, or proceeds with the rebound of the hydroxyl group return to the solvent cage to form the hydroxylated product. While in the C=C bond activation, 1 is a normal oxygen donor and shows two-state reactivity to present the epoxide product via a direct oxygen atom transfer mechanism. These mechanistic findings fit and explain the famous Valentine’s experiments and enrich the non-rebound scenario in bioinorganic chemistry.

关键词： Reaction mechanism DFT calculations Metal-iodosylbenzene Ritter reaction Olefin oxidation

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过氧化氢生产与利用的新进展

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Chinese Journal of Catalysis 2021年第8期42卷 1241-1252页

作者： Shunichi Fukuzumi Yong-Min Lee wonwoo nam 梨花女子大学化学与纳米科学系首尔韩国美珠大学科学与工程研究生院名古屋日本梨花女子大学基础科学研究院首尔韩国

过氧化氢既可用作环境友好的绿色氧化剂,也可用作燃料电池中的太阳能燃料,因而受到越来越多的关注.本文综述了太阳能驱动分子氧氧化水制备过氧化氢及其作为绿色氧化剂和燃料的研究进展.利用太阳能将水的e^(-)和4e^(-)氧化与分子氧的e^(-... 详细信息

过氧化氢既可用作环境友好的绿色氧化剂,也可用作燃料电池中的太阳能燃料,因而受到越来越多的关注.本文综述了太阳能驱动分子氧氧化水制备过氧化氢及其作为绿色氧化剂和燃料的研究进展.利用太阳能将水的e^(-)和4e^(-)氧化与分子氧的e^(-)还原相结合,使光催化生产过氧化氢成为可能;本文讨论了与e^(-)和4e^(-)水氧化选择性及e^(-)和4e^(-)氧还原选择性相关的催化反应控制.由于光催化e^(-)氧化水和e^(-)还原分子氧的过程都产生过氧化氢,因此该组合的催化效率较高.太阳能光驱动水氧化及分子氧还原生产过氧化氢与过氧化氢催化氧化底物相结合,在该过程中分子氧用作最环保的氧化剂.

关键词：过氧化氢生产水氧化分子氧还原光催化氧化反应动力学与机理

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MONONUCLEAR NON-HEME IRON（IV）-OXO COMPLEXES IN OXYGENATION REACTIONS

MONONUCLEAR NON-HEME IRON（IV）-OXO COMPLEXES IN OXYGENATION...

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中国化学会第26届学术年会无机与配位化学分会场

作者： wonwoo nam Department of Chemistry Division of Nano Sciences and Center for Biomimetic Systems Ewha Womans University Seoul 120-750 Korea

＜正＞Mononuclear nonheme iron enzymes comprise an important group of dioxygen-activating enzymes that are involved in many metabolically important oxidative transformations. The

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A Mononuclear Nonheme Cobalt(Ⅳ)-Oxo Complex:Photocatalytic and Chemical Synthesis,Spectroscopic Characterization,and Reactivity Studies

A Mononuclear Nonheme Cobalt(Ⅳ)-Oxo Complex:Photocatalytic ...

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中国化学会第十二届全国物理有机化学学术会议

作者： Bin Wang Wei Sun wonwoo nam Department of Chemistry and Chemical Engineering University of Jinan Lanzhou Institute of Chemical Physics Chinese Academy of Sciences Center for Biomimetic Systems Ewha Womans University

Terminal cobalt(Ⅳ)-oxo(Co

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Catalpa bignonioides extract improves exercise performance through regulation of growth and metabolism in skeletal muscles

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Asian Pacific Journal of Tropical Biomedicine 2024年第2期14卷 47-54页

作者： Hoibin Jeong Dong-joo Lee Sung-Pil Kwon SeonJu Park Song-Rae Kim Seung Hyun Kim Jae-Il Park Deug-chan Lee Kyung-Min Choi wonwoo Lee Ji-Won Park Bohyun Yun Su-Hyeon Cho Kil-nam Kim Seoul Center Korea Basic Science InstituteSeoul 02841Republic of Korea Chuncheon Center Korea Basic Science InstituteChuncheon 24341Republic of Korea Research&Development Center Chungdam CDC JNPharm LLC.Chuncheon 24341Republic of Korea Department of Biomedical Technology Kangwon National UniversityChuncheon 24341Republic of Korea Yonsei Institute of Pharmaceutical Sciences College of PharmacyYonsei UniversityIncheon 21983Republic of Korea Gwangju Center Korea Basic Science InstituteGwangju 61751Republic of Korea Honam National Institute of Biological Resources 99Gohadoan-gilMokpo-siJeollanam-do58762Republic of Korea Department of Bio-analysis Science University of Science&TechnologyDaejeon34113Republic of Korea

Objective:To evaluate the effects of Catalpa bignonioides fruit extract on the promotion of muscle growth and muscular capacity in vitro and in vivo.Methods:Cell viability was measured using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.Cell proliferation was assessed using a 5-bromo-2’-deoxyuridine(BrdU)assay kit.Western blot analysis was performed to determine the protein expressions of related factors.The effects of Catalpa bignonioides extract were investigated in mice using the treadmill exhaustion test and whole-limb grip strength assay.Chemical composition analysis was performed using high-performance liquid chromatography(HPLC).Results:Catalpa bignonioides extract increased the proliferation of C2C12 mouse myoblasts by activating the Akt/mTOR signaling pathway.It also induced metabolic changes,increasing the number of mitochondria and glucose metabolism by phosphorylating adenosine monophosphate-activated protein kinase.In an in vivo study,the extract-treated mice showed improved motor abilities,such as muscular endurance and grip strength.Additionally,HPLC analysis showed that vanillic acid may be the main component of the Catalpa bignonioides extract that enhanced muscle strength.Conclusions:Catalpa bignonioides improves exercise performance through regulation of growth and metabolism in skeletal muscles,suggesting its potential as an effective natural agent for improving muscular strength.

关键词： Catalpa bignonioides Skeletal muscle Cell proliferation Mitochondria Energy metabolism C2C12

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