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  1. Article ; Online: Synthetic Efforts toward Lannotinidine G Based on an Aziridinium-Mediated Ring Contraction and Dienyne Metathesis.

    Peitsinis, Zisis / Trauner, Dirk

    Organic letters

    2024  Volume 26, Issue 15, Page(s) 3184–3188

    Abstract: Lannotinidine G is a unique Lycopodium alkaloid that features a tricyclic [6/6/6] core with 3 contiguous stereocenters and a 1,3-diene moiety in addition to a 7-membered lactone. Herein, we disclose our efforts toward the synthesis of this natural ... ...

    Abstract Lannotinidine G is a unique Lycopodium alkaloid that features a tricyclic [6/6/6] core with 3 contiguous stereocenters and a 1,3-diene moiety in addition to a 7-membered lactone. Herein, we disclose our efforts toward the synthesis of this natural product, which achieved the construction of the aza-tricyclic core with the correct configuration at its three stereocenters. Key features of our strategy include a highly diastereoselective Fráter-Seebach alkylation and Corey-Chaykovsky type epoxide formation, an unusual aziridinium-mediated ring contraction for the formation of the piperidine moiety, and a regioselective dienyne metathesis.
    Language English
    Publishing date 2024-04-02
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.4c00791
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Complex Natural Products Derived from Pyrogallols.

    Novak, Alexander J E / Trauner, Dirk

    Progress in the chemistry of organic natural products

    2022  Volume 118, Page(s) 1–46

    Abstract: Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and ... ...

    Abstract Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.
    MeSH term(s) Biological Products ; Cycloaddition Reaction ; Pyrogallol ; Quinones
    Chemical Substances Biological Products ; Quinones ; Pyrogallol (01Y4A2QXY0)
    Language English
    Publishing date 2022-04-13
    Publishing country Austria
    Document type Journal Article
    ISSN 2191-7043
    ISSN 2191-7043
    DOI 10.1007/978-3-030-92030-2_1
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  3. Article ; Online: Concise Synthesis of Glycerophospholipids.

    Mukhopadhyay, Tufan K / Trauner, Dirk

    The Journal of organic chemistry

    2022  Volume 88, Issue 15, Page(s) 11253–11257

    Abstract: Glycerophospholipids are major components of cellular membranes and provide important signaling molecules. Besides shaping membrane properties, some bind to specific receptors to activate biological pathways. Untangling the roles of individual ... ...

    Abstract Glycerophospholipids are major components of cellular membranes and provide important signaling molecules. Besides shaping membrane properties, some bind to specific receptors to activate biological pathways. Untangling the roles of individual glycerophospholipids requires clearly defined molecular species, a challenge that can be best addressed through chemical synthesis. However, glycerophospholipid syntheses are often lengthy due to the contrasting polarities found within these lipids. We now report a general strategy to quickly access glycerophospholipids via opening of a phosphate triester epoxide with carboxylic acids catalyzed by Jacobsen's Co(salen) complex. We show that this method can be applied to a variety of commercially available fatty acids, photoswitchable fatty acids, and other carboxylic acids to provide the corresponding glycerophosphate derivatives.
    MeSH term(s) Glycerophospholipids/chemistry ; Glycerophospholipids/metabolism ; Fatty Acids ; Cell Membrane/metabolism ; Carboxylic Acids/metabolism
    Chemical Substances Glycerophospholipids ; Fatty Acids ; Carboxylic Acids
    Language English
    Publishing date 2022-11-30
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c02096
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    Zs.A 4473: Show issues Location:
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  4. Article ; Online: The Chemist and the Architect.

    Trauner, Dirk

    Angewandte Chemie (International ed. in English)

    2017  Volume 57, Issue 16, Page(s) 4177–4191

    Abstract: To imagine a structure and then express it in material form is one of the most satisfying of human activities. It is pervasive throughout the arts and crafts and it is one of the defining features of architecture. It is also at the heart of synthetic ... ...

    Abstract To imagine a structure and then express it in material form is one of the most satisfying of human activities. It is pervasive throughout the arts and crafts and it is one of the defining features of architecture. It is also at the heart of synthetic chemistry.
    Language English
    Publishing date 2017-12-27
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201708325
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  5. Article ; Online: Author Correction: Natural product anticipation through synthesis.

    Hetzler, Belinda E / Trauner, Dirk / Lawrence, Andrew L

    Nature reviews. Chemistry

    2022  Volume 6, Issue 3, Page(s) 232

    Language English
    Publishing date 2022-01-20
    Publishing country England
    Document type Published Erratum
    ISSN 2397-3358
    ISSN (online) 2397-3358
    DOI 10.1038/s41570-022-00374-w
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  6. Article: Optical Control of Glycerolipids and Sphingolipids.

    Trauner, Dirk / Morstein, Johannes

    Chimia

    2021  Volume 75, Issue 12, Page(s) 1022–1025

    Abstract: Glycerolipids, sphingolipids, and sterols are the three major classes of membrane lipids. Both glycerolipids and sphingolipids are comprised of combinations of polar headgroups and fatty acid tails. The fatty acid tail can be chemically modified with an ... ...

    Abstract Glycerolipids, sphingolipids, and sterols are the three major classes of membrane lipids. Both glycerolipids and sphingolipids are comprised of combinations of polar headgroups and fatty acid tails. The fatty acid tail can be chemically modified with an azobenzene photoswitch giving rise to photoswitchable lipids. This approach has yielded a number of photopharmacological tools that allow for the control various of aspects of lipid assembly, metabolism, and physiology with light.
    MeSH term(s) Sphingolipids
    Chemical Substances Sphingolipids
    Language English
    Publishing date 2021-12-18
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1516-7
    ISSN 0009-4293
    ISSN 0009-4293
    DOI 10.2533/chimia.2021.1022
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    In stock of ZB MED Bonn / Germany

    Z 4.5: Show issues

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  7. Article: A Conversation with Gerhard Bringmann.

    Trauner, Dirk / Roßmann, Kilian

    ACS central science

    2020  Volume 6, Issue 8, Page(s) 1248–1252

    Language English
    Publishing date 2020-08-06
    Publishing country United States
    Document type Editorial
    ISSN 2374-7943
    ISSN 2374-7943
    DOI 10.1021/acscentsci.0c00388
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  8. Article ; Online: Optical control of targeted protein degradation.

    Reynders, Martin / Trauner, Dirk

    Cell chemical biology

    2021  Volume 28, Issue 7, Page(s) 969–986

    Abstract: Molecular glues and proteolysis targeting chimeras (PROTACs) have emerged as small-molecule tools that selectively induce the degradation of a chosen protein and have shown therapeutic promise. Recently, several approaches employing light as an ... ...

    Abstract Molecular glues and proteolysis targeting chimeras (PROTACs) have emerged as small-molecule tools that selectively induce the degradation of a chosen protein and have shown therapeutic promise. Recently, several approaches employing light as an additional stimulus to control induced protein degradation have been reported. Here, we analyze the principles guiding the design of such systems, provide a survey of the literature published to date, and discuss opportunities for further development. Light-responsive degraders enable the precise temporal and spatial control of protein levels, making them useful research tools but also potential candidates for human precision medicine.
    MeSH term(s) Humans ; Precision Medicine ; Proteins/antagonists & inhibitors ; Proteins/metabolism ; Proteolysis/drug effects ; Small Molecule Libraries/chemistry ; Small Molecule Libraries/pharmacology
    Chemical Substances Proteins ; Small Molecule Libraries
    Language English
    Publishing date 2021-06-10
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Review
    ISSN 2451-9448
    ISSN (online) 2451-9448
    DOI 10.1016/j.chembiol.2021.05.010
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  9. Article ; Online: PHOTACs Enable Optical Control of Protein Degradation.

    Reynders, Martin / Trauner, Dirk

    Methods in molecular biology (Clifton, N.J.)

    2021  Volume 2365, Page(s) 315–329

    Abstract: Proteolysis Targeting Chimeras (PROTACs) are a promising technology to degrade specific target proteins. As bifunctional small molecules, PROTACs induce the ternary complex formation between an E3 ligase and a protein of interest (POI), leading to ... ...

    Abstract Proteolysis Targeting Chimeras (PROTACs) are a promising technology to degrade specific target proteins. As bifunctional small molecules, PROTACs induce the ternary complex formation between an E3 ligase and a protein of interest (POI), leading to polyubiquitylation and subsequent proteasomal degradation of the protein in a catalytic fashion. We have developed a strategy to control PROTACs with the spatiotemporal precision of light, which led to light-activated versions, termed PHOTACs (PHOtochemically TArgeted Chimeras). By incorporating an azobenzene photoswitch into the PROTAC, we can reversibly control degradation of the POI, as demonstrated for BRD2-4 and FKBP12. Here, we describe our modular approach and the application of PHOTACs for the optical control of protein levels in detail. PHOTACs hold promise as both research tools and precision pharmaceutics.
    MeSH term(s) Proteolysis ; Ubiquitin-Protein Ligases/genetics ; Ubiquitin-Protein Ligases/metabolism
    Chemical Substances Ubiquitin-Protein Ligases (EC 2.3.2.27)
    Language English
    Publishing date 2021-08-25
    Publishing country United States
    Document type Journal Article
    ISSN 1940-6029
    ISSN (online) 1940-6029
    DOI 10.1007/978-1-0716-1665-9_17
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  10. Article ; Online: Photopharmacological control of cell signaling with photoswitchable lipids.

    Mukhopadhyay, Tufan K / Morstein, Johannes / Trauner, Dirk

    Current opinion in pharmacology

    2022  Volume 63, Page(s) 102202

    Abstract: Many aspects of cell signaling are controlled by lipids. Several signaling lipids have been functionalized with an azobenzene photoswitch to control underlying signaling dynamics with light. Herein, we provide an overview of signaling photolipids ... ...

    Abstract Many aspects of cell signaling are controlled by lipids. Several signaling lipids have been functionalized with an azobenzene photoswitch to control underlying signaling dynamics with light. Herein, we provide an overview of signaling photolipids developed to date focusing on their biological applications. These include immunomodulation, kinase translocation, apoptosis, ion channel activation, G-protein coupled receptor activation, and neurogenesis.
    MeSH term(s) Humans ; Lipids ; Receptors, G-Protein-Coupled ; Signal Transduction
    Chemical Substances Lipids ; Receptors, G-Protein-Coupled
    Language English
    Publishing date 2022-03-09
    Publishing country England
    Document type Journal Article ; Review ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 2037057-X
    ISSN 1471-4973 ; 1471-4892
    ISSN (online) 1471-4973
    ISSN 1471-4892
    DOI 10.1016/j.coph.2022.102202
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 5608: Show issues Location:
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