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  1. Article ; Online: Alternatives to Iridium: A Polyaza[7]helicene as a Strongly Reductive Visible Light Photoredox Catalyst.

    Rocker, Johannes / Opatz, Till

    ACS organic & inorganic Au

    2022  Volume 2, Issue 5, Page(s) 415–421

    Abstract: The use of a readily accessible polyazahelicene as a strongly reducing metal-free alternative to the commonly used precious metal based photoredox catalysts is demonstrated. An improved two-step synthesis of the catalyst is described, and its ... ...

    Abstract The use of a readily accessible polyazahelicene as a strongly reducing metal-free alternative to the commonly used precious metal based photoredox catalysts is demonstrated. An improved two-step synthesis of the catalyst is described, and its photophysical properties with respect to its use as a photoredox catalyst are evaluated. Its activity under visible light irradiation is proven by application in two double radical light-driven multicomponent reactions. The azahelicene gave comparable results to an iridium-based catalyst originally used for the same transformations.
    Language English
    Publishing date 2022-07-13
    Publishing country United States
    Document type Journal Article
    ISSN 2694-247X
    ISSN (online) 2694-247X
    DOI 10.1021/acsorginorgau.2c00022
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Reversible oxidative dimerization of 4-thiouridines in tRNA isolates.

    Bessler, Larissa / Groß, Jonathan / Kampf, Christopher J / Opatz, Till / Helm, Mark

    RSC chemical biology

    2024  Volume 5, Issue 3, Page(s) 216–224

    Abstract: The occurrence of non-canonical nucleoside structures in RNA of biological or synthetic origin has encountered several recent boosts in attention, namely in the context of RNA modifications, and with an eye to RNA vaccines. New nucleoside structures ... ...

    Abstract The occurrence of non-canonical nucleoside structures in RNA of biological or synthetic origin has encountered several recent boosts in attention, namely in the context of RNA modifications, and with an eye to RNA vaccines. New nucleoside structures introduce added functionality and function into biopolymers that are otherwise rather homogenous in their chemical structure. Here, we report the discovery of a presumed RNA modification that was identified by combination of liquid chromatography-tandem mass spectrometry (LC-MS/MS) with stable isotope labelling as a dimer of the known RNA modification 4-thiouridine (s
    Language English
    Publishing date 2024-02-01
    Publishing country England
    Document type Journal Article
    ISSN 2633-0679
    ISSN (online) 2633-0679
    DOI 10.1039/d3cb00221g
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  3. Article ; Online: Total Synthesis of (±)-Oxacyclododecindione.

    Seipp, Kevin / Grölz, Vincent / Glass, Hagen / Quraishi, Elisabeth / Vierengel, Nina / Opatz, Till

    The Journal of organic chemistry

    2024  Volume 89, Issue 8, Page(s) 5746–5763

    Abstract: Racemic total synthesis of the natural product oxacyclododecindione, isolated in 2008 as the first member of the oxacyclododecindione family, is reported. Studies toward this molecule commenced with a biomimetic late-stage C-H oxidation starting from 14- ... ...

    Abstract Racemic total synthesis of the natural product oxacyclododecindione, isolated in 2008 as the first member of the oxacyclododecindione family, is reported. Studies toward this molecule commenced with a biomimetic late-stage C-H oxidation starting from 14-deoxyoxacyclododecindione as a known precursor. This provided insights into the reactivity of the macrolactone class but did not permit the synthesis of the target natural product. Based on these results, a synthetic strategy through intramolecular Friedel-Crafts acylation combined with Barton decarboxylation to introduce the tertiary alcohol, a major challenge in previous synthetic efforts, was envisioned. This resulted in an 11-step racemic total synthesis of (±)-oxacyclododecindione, renowned for its potent anti-inflammatory and antifibrotic activities.
    MeSH term(s) Anti-Inflammatory Agents ; Macrocyclic Compounds ; Acylation ; Biological Products
    Chemical Substances oxacyclododecindione ; Anti-Inflammatory Agents ; Macrocyclic Compounds ; Biological Products
    Language English
    Publishing date 2024-04-10
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.4c00333
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  4. Article ; Online: Total synthesis of lamellarin G trimethyl ether through enaminone cyclocondensation.

    Šachlevičiūtė, Urtė / Kleizienė, Neringa / Bieliauskas, Aurimas / Šačkus, Algirdas / Opatz, Till

    Organic & biomolecular chemistry

    2023  Volume 21, Issue 29, Page(s) 5997–6007

    Abstract: A synthesis of pyrrolo[2,1- ...

    Abstract A synthesis of pyrrolo[2,1-
    Language English
    Publishing date 2023-07-26
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d3ob00870c
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  5. Article ; Online: Discovery and characterisation of a broderol-like illudin, omphaderol in the mycelial extracts of Omphalotus mexicanus (Omphalotaceae) using UPLC-QTOF-MS and NMR spectroscopy.

    Eckhardt, Paul / Reinecke, Silke / Opatz, Till / Stadler, Marc / Sandargo, Birthe

    Phytochemical analysis : PCA

    2023  Volume 35, Issue 3, Page(s) 469–475

    Abstract: Introduction: The genus Omphalotus, in particular the "Jack-O'Lantern mushrooms" Omphalotus illudens and Omphalotus olearius, are famous for the production of the DNA-alkylating illudins. A lesser-known species, Omphalotus mexicanus, native to Central ... ...

    Abstract Introduction: The genus Omphalotus, in particular the "Jack-O'Lantern mushrooms" Omphalotus illudens and Omphalotus olearius, are famous for the production of the DNA-alkylating illudins. A lesser-known species, Omphalotus mexicanus, native to Central America, also produces cytotoxic illudins S and M, but its minor secondary metabolites are yet to be investigated.
    Objective: To identify, isolate, and elucidate the structure of novel secondary metabolites of the illudin family in mycelial extracts of O. mexicanus from submerse cultivation.
    Methodology: A fermentation of the fungus in 15 L stirred tank bioreactors is described. Mycelial extracts were separated using a combination of flash chromatography with preparative RP-C18 high-performance liquid chromatography (HPLC). Analysis of metabolites was done using an ultrahigh-performance liquid chromatography ultraviolet diode array detector (UPLC-UV-DAD) system coupled to an electrospray ionisation quadrupole time-of-flight (ESI-QTOF) mass spectrometer. Structures were elucidated using one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance spectroscopy (NMR) techniques followed by comparison of experimental and simulated electronic circular dichroism (ECD) spectra to determine absolute configurations.
    Results: Two novel illudin derivatives, for which we propose the names omphaderol (1) and illudaneol B (2), as well as illudaneol (3) and the unusual cyclobutylcyclopentane illudosin (4), were isolated from the mycelia and characterised.
    Conclusion: Particularly the illudaneol derivatives with their high titers may be potential building blocks for an alternative semisynthetic route to new illudin derivatives with improved medical properties. Additionally, the findings improve the knowledge of minor illudin compounds in the mycelial extract of this fungus and may be of significance for future biosynthetic studies of the illudins.
    MeSH term(s) Chromatography, High Pressure Liquid ; Chromatography, Liquid/methods ; Mass Spectrometry ; Magnetic Resonance Spectroscopy ; Spectrometry, Mass, Electrospray Ionization/methods ; Agaricales
    Language English
    Publishing date 2023-11-03
    Publishing country England
    Document type Journal Article
    ZDB-ID 1073576-8
    ISSN 1099-1565 ; 0958-0344
    ISSN (online) 1099-1565
    ISSN 0958-0344
    DOI 10.1002/pca.3301
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4608: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  6. Book ; Online ; Thesis: Synthese und Evaluierung von neuen Cystein-Proteaseinhibitoren und Inhibitoren der Afrikanischen Trypanosomiasis

    Klein, Philipp Peter [Verfasser] / Opatz, Till [Akademischer Betreuer]

    2023  

    Author's details Philipp Peter Klein ; Betreuer: Till Opatz
    Keywords Naturwissenschaften ; Science
    Subject code sg500
    Language German
    Publisher Universitätsbibliothek der Johannes Gutenberg-Universität Mainz
    Publishing place Mainz
    Document type Book ; Online ; Thesis
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  7. Book ; Online ; Thesis: Cyanid als C1-Baustein in der organischen Synthese - Nachhaltige Freisetzung und Anwendung in der Synthese diverser Heterozyklen

    Grundke, Caroline Verfasser] / [Opatz, Till [Akademischer Betreuer]

    2023  

    Author's details Caroline Grundke ; Betreuer: Till Opatz
    Keywords Naturwissenschaften ; Science
    Subject code sg500
    Language German
    Publisher Universitätsbibliothek der Johannes Gutenberg-Universität Mainz
    Publishing place Mainz
    Document type Book ; Online ; Thesis
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  8. Book ; Online ; Thesis: Synthese funktionalisierter Makrolactone für den Einsatz in der Targetidentifizierung und Aufklärung und Synthese biologisch-aktiver Naturstoffe

    Vierengel, Nina Anke [Verfasser] / Opatz, Till [Akademischer Betreuer]

    2023  

    Author's details Nina Anke Vierengel ; Betreuer: Till Opatz
    Keywords Medizin, Gesundheit ; Medicine, Health
    Subject code sg610
    Language German
    Publisher Universitätsbibliothek der Johannes Gutenberg-Universität Mainz
    Publishing place Mainz
    Document type Book ; Online ; Thesis
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  9. Article ; Online: Vinylcyclopropane [3+2] Cycloaddition with Acetylenic Sulfones Based on Visible Light Photocatalysis.

    Luque, Adriana / Groß, Jonathan / Zähringer, Till J B / Kerzig, Christoph / Opatz, Till

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2022  Volume 28, Issue 18, Page(s) e202104329

    Abstract: The first intermolecular visible light [3+2] cycloaddition reaction performed on a meta photocycloadduct employing acetylenic sulfones is described. The developed methodology exploits the advantages of combining UV and visible-light in a two-step ... ...

    Abstract The first intermolecular visible light [3+2] cycloaddition reaction performed on a meta photocycloadduct employing acetylenic sulfones is described. The developed methodology exploits the advantages of combining UV and visible-light in a two-step sequence that provides a photogenerated cyclopropane which, through a strain-release process, generates a new cyclopentane ring while significantly increasing the molecular complexity. Mechanistic studies and DFT calculations indicate an energy transfer pathway for the visible light-driven reaction step. This strategy could be extended to simpler vinylcyclopropanes.
    MeSH term(s) Acetylene ; Alkynes ; Cycloaddition Reaction ; Light ; Sulfones
    Chemical Substances Alkynes ; Sulfones ; Acetylene (OC7TV75O83)
    Language English
    Publishing date 2022-03-04
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202104329
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  10. Article ; Online: NMR and Docking Calculations Reveal Novel Atomistic Selectivity of a Synthetic High-Affinity Free Fatty Acid vs. Free Fatty Acids in Sudlow's Drug Binding Sites in Human Serum Albumin.

    Venianakis, Themistoklis / Primikyri, Alexandra / Opatz, Till / Petry, Stefan / Papamokos, Georgios / Gerothanassis, Ioannis P

    Molecules (Basel, Switzerland)

    2023  Volume 28, Issue 24

    Abstract: Saturation transfer difference (STD), inter-ligand NOEs (INPHARMA NMR), and docking calculations are reported for investigating specific binding sites of the high-affinity synthetic 7-nitrobenz-2-oxa-1,3-diazoyl-4- ... ...

    Abstract Saturation transfer difference (STD), inter-ligand NOEs (INPHARMA NMR), and docking calculations are reported for investigating specific binding sites of the high-affinity synthetic 7-nitrobenz-2-oxa-1,3-diazoyl-4-C
    MeSH term(s) Humans ; Serum Albumin, Human/chemistry ; Fatty Acids, Nonesterified ; Serum Albumin/chemistry ; Ibuprofen ; Protein Binding ; Warfarin ; Binding Sites ; Fatty Acids/metabolism ; Magnetic Resonance Spectroscopy ; Amino Acids/metabolism
    Chemical Substances Serum Albumin, Human (ZIF514RVZR) ; Fatty Acids, Nonesterified ; Serum Albumin ; Ibuprofen (WK2XYI10QM) ; Warfarin (5Q7ZVV76EI) ; Fatty Acids ; Amino Acids
    Language English
    Publishing date 2023-12-07
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules28247991
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    Zs.MO 81: Show issues

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