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  1. Article ; Online: Redox-Active Organic Materials: From Energy Storage to Redox Catalysis.

    Kim, Jaehwan / Ling, Jianheng / Lai, Yihuan / Milner, Phillip J

    ACS materials Au

    2024  Volume 4, Issue 3, Page(s) 258–273

    Abstract: Electroactive materials are central to myriad applications, including energy storage, sensing, and catalysis. Compared to traditional inorganic electrode materials, redox-active organic materials such as porous organic polymers (POPs) and covalent ... ...

    Abstract Electroactive materials are central to myriad applications, including energy storage, sensing, and catalysis. Compared to traditional inorganic electrode materials, redox-active organic materials such as porous organic polymers (POPs) and covalent organic frameworks (COFs) are emerging as promising alternatives due to their structural tunability, flexibility, sustainability, and compatibility with a range of electrolytes. Herein, we discuss the challenges and opportunities available for the use of redox-active organic materials in organoelectrochemistry, an emerging area in fine chemical synthesis. In particular, we highlight the utility of organic electrode materials in photoredox catalysis, electrochemical energy storage, and electrocatalysis and point to new directions needed to unlock their potential utility for organic synthesis. This Perspective aims to bring together the organic, electrochemistry, and polymer communities to design new heterogeneous electrocatalysts for the sustainable synthesis of complex molecules.
    Language English
    Publishing date 2024-01-12
    Publishing country United States
    Document type Journal Article ; Review
    ISSN 2694-2461
    ISSN (online) 2694-2461
    DOI 10.1021/acsmaterialsau.3c00096
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Structures of chloramphenicol acetyltransferase III and Escherichia coli β-ketoacylsynthase III co-crystallized with partially hydrolysed acetyl-oxa(dethia)CoA.

    Benjamin, Aaron B / Stunkard, Lee M / Ling, Jianheng / Nice, Jaelen N / Lohman, Jeremy R

    Acta crystallographica. Section F, Structural biology communications

    2023  Volume 79, Issue Pt 3, Page(s) 61–69

    Abstract: Acetyl coenzyme A (acetyl-CoA) is a reactive metabolite that nonproductively hydrolyzes in a number of enzyme active sites in the crystallization time frame. In order to elucidate the enzyme-acetyl-CoA interactions leading to catalysis, acetyl-CoA ... ...

    Abstract Acetyl coenzyme A (acetyl-CoA) is a reactive metabolite that nonproductively hydrolyzes in a number of enzyme active sites in the crystallization time frame. In order to elucidate the enzyme-acetyl-CoA interactions leading to catalysis, acetyl-CoA substrate analogs are needed. One possible analog for use in structural studies is acetyl-oxa(dethia)CoA (AcOCoA), in which the thioester S atom of CoA is replaced by an O atom. Here, structures of chloramphenicol acetyltransferase III (CATIII) and Escherichia coli ketoacylsynthase III (FabH) from crystals grown in the presence of partially hydrolyzed AcOCoA and the respective nucleophile are presented. Based on the structures, the behavior of AcOCoA differs between the enzymes, with FabH reacting with AcOCoA and CATIII being unreactive. The structure of CATIII reveals insight into the catalytic mechanism, with one active site of the trimer having relatively clear electron density for AcOCoA and chloramphenicol and the other active sites having weaker density for AcOCoA. One FabH structure contains a hydrolyzed AcOCoA product oxa(dethia)CoA (OCoA), while the other FabH structure contains an acyl-enzyme intermediate with OCoA. Together, these structures provide preliminary insight into the use of AcOCoA for enzyme structure-function studies with different nucleophiles.
    MeSH term(s) Acetyl Coenzyme A ; Chloramphenicol O-Acetyltransferase ; Crystallography, X-Ray ; Catalysis ; Escherichia coli/genetics
    Chemical Substances Acetyl Coenzyme A (72-89-9) ; Chloramphenicol O-Acetyltransferase (EC 2.3.1.28)
    Language English
    Publishing date 2023-02-23
    Publishing country United States
    Document type Journal Article
    ISSN 2053-230X
    ISSN (online) 2053-230X
    DOI 10.1107/S2053230X23001206
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Catalytic Synthesis of Conjugated Azopolymers from Aromatic Diazides.

    Andjaba, John M / Rybak, Christopher J / Wang, Zhiyang / Ling, Jianheng / Mei, Jianguo / Uyeda, Christopher

    Journal of the American Chemical Society

    2021  Volume 143, Issue 10, Page(s) 3975–3982

    Abstract: Conjugated polymers containing main chain azoarene repeat units are synthesized by a dinickel catalyzed N=N coupling reaction of aromatic diazides. The polymerization exhibits broad substrate scope and is compatible with heterocycles commonly featured in ...

    Abstract Conjugated polymers containing main chain azoarene repeat units are synthesized by a dinickel catalyzed N=N coupling reaction of aromatic diazides. The polymerization exhibits broad substrate scope and is compatible with heterocycles commonly featured in high performance organic materials, including carbazole, thiophene, propylenedioxythiophene (ProDOT), diketopyrrolopyrrole (DPP), and isoindigo. Copolymerizations can be carried out using monomer mixtures, and monoazide chain stoppers can be used to install well-defined end groups. Azopolymers possess unique properties owing to the functionality of the azo linkages. For example, protonation at nitrogen results in LUMO lowering and red-shifted absorption bands. Additionally, N=N bonds possess low-lying π* levels, allowing azopolymers to be reversibly reduced under mild conditions.
    Language English
    Publishing date 2021-03-04
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.1c00447
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

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  4. Article ; Online: Activity of Fatty Acid Biosynthesis Initiating Ketosynthase FabH with Acetyl/Malonyl-oxa/aza(dethia)CoAs.

    Boram, Trevor J / Benjamin, Aaron B / Silva de Sousa, Amanda / Stunkard, Lee M / Stewart, Taylor A / Adams, Timothy J / Craft, Nicholas A / Velázquez-Marrero, Kevin G / Ling, Jianheng / Nice, Jaelen N / Lohman, Jeremy R

    ACS chemical biology

    2023  Volume 18, Issue 1, Page(s) 49–58

    Abstract: Fatty acid and polyketide biosynthetic enzymes exploit the reactivity of acyl- and malonyl-thioesters for catalysis. A prime example is FabH, which initiates fatty acid biosynthesis in many bacteria and plants. FabH performs an acyltransferase reaction ... ...

    Abstract Fatty acid and polyketide biosynthetic enzymes exploit the reactivity of acyl- and malonyl-thioesters for catalysis. A prime example is FabH, which initiates fatty acid biosynthesis in many bacteria and plants. FabH performs an acyltransferase reaction with acetyl-CoA to generate an acetyl-
    MeSH term(s) Acetyl Coenzyme A/metabolism ; Acyltransferases/genetics ; Acyltransferases/metabolism ; Acyl Carrier Protein/chemistry ; Malonyl Coenzyme A/metabolism ; Fatty Acids ; Polyketides ; 3-Oxoacyl-(Acyl-Carrier-Protein) Synthase
    Chemical Substances Acetyl Coenzyme A (72-89-9) ; Acyltransferases (EC 2.3.-) ; Acyl Carrier Protein ; Malonyl Coenzyme A (524-14-1) ; Fatty Acids ; Polyketides ; 3-Oxoacyl-(Acyl-Carrier-Protein) Synthase (EC 2.3.1.41)
    Language English
    Publishing date 2023-01-10
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ISSN 1554-8937
    ISSN (online) 1554-8937
    DOI 10.1021/acschembio.2c00667
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Emissive Substoichiometric Covalent Organic Frameworks for Water Sensing and Harvesting.

    Maiti, Sayan / Sharma, Jatan K / Ling, Jianheng / Tietje-Mckinney, Dylan / Heaney, Matthew P / Runčevski, Tomče / Addicoat, Matthew A / D'Souza, Francis / Milner, Phillip J / Das, Anindita

    Macromolecular rapid communications

    2022  Volume 44, Issue 11, Page(s) e2200751

    Abstract: Emissive covalent organic frameworks (COFs) have recently emerged as next-generation porous materials with attractive properties such as tunable topology, porosity, and inherent photoluminescence. Among the different types of COFs, substoichiometric ... ...

    Abstract Emissive covalent organic frameworks (COFs) have recently emerged as next-generation porous materials with attractive properties such as tunable topology, porosity, and inherent photoluminescence. Among the different types of COFs, substoichiometric frameworks (so-called Type III COFs) are especially attractive due to the possibility of not only generating unusual topology and complex pore architectures but also facilitating the introduction of well-defined functional groups at precise locations for desired functions. Herein, the first example of a highly emissive (PLQY 6.8%) substoichiometric 2D-COF (COF-SMU-1) featuring free uncondensed aldehyde groups is reported. In particular, COF-SMU-1 features a dual-pore architecture with an overall bex net topology, tunable emission in various organic solvents, and distinct colorimetric changes in the presence of water. To gain further insights into its photoluminescence properties, the charge transfer, excimer emission, and excited state exciton dynamics of COF-SMU-1 are investigated using femtosecond transient absorption spectroscopy in different organic solvents. Additionally, highly enhanced atmospheric water-harvesting properties of COF-SMU-1 are revealed using FT-IR and water sorption studies.The findings will not only lead to in-depth understanding of structure-property relationships in emissive COFs but also open new opportunities for designing COFs for potential applications in solid-state lighting and water harvesting.
    MeSH term(s) Water ; Metal-Organic Frameworks ; Spectroscopy, Fourier Transform Infrared ; Aldehydes ; Solvents
    Chemical Substances Water (059QF0KO0R) ; Metal-Organic Frameworks ; Aldehydes ; Solvents
    Language English
    Publishing date 2022-12-07
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1475027-2
    ISSN 1521-3927 ; 1022-1336
    ISSN (online) 1521-3927
    ISSN 1022-1336
    DOI 10.1002/marc.202200751
    Database MEDical Literature Analysis and Retrieval System OnLINE

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