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DDC: 660 × Type: Article × Publisher: Washington, DC : ACS Publications × WGL Institute: INP ×

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    Ring-Closure Mechanisms Mediated by Laccase to Synthesize Phenothiazines, Phenoxazines, and Phenazines
    (Washington, DC : ACS Publications, 2020) Hahn, Veronika; Mikolasch, Annett; Weitemeyer, Josephine; Petters, Sebastian; Davids, Timo; Lalk, Michael; Lackmann, Jan-Wilm; Schauer, Frieder
    The green and environmentally friendly synthesis of highly valuable organic substances is one possibility for the utilization of laccases (EC 1.10.3.2). As reactants for the herein described syntheses, different o-substituted arylamines or arylthiols and 2,5-dihydroxybenzoic acid and its derivatives were used. In this way, the formation of phenothiazines, phenoxazines, and phenazines was achieved in aqueous solution mediated by the laccase of Pycnoporus cinnabarinus in the presence of oxygen. Two types of phenothiazines (3-hydroxy- and 3-oxo-phenothiazines) formed in one reaction assay were described for the first time. The cyclization reactions yielded C–N, C–S, or C–O bonds. The syntheses were investigated with regard to the substitution pattern of the reaction partners. Differences in C–S and C–N bond formations without cyclization are discussed.
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    D-Glucose Oxidation by Cold Atmospheric Plasma-Induced Reactive Species
    (Washington, DC : ACS Publications, 2022) Ahmadi, Mohsen; Nasri, Zahra; von Woedtke, Thomas; Wende, Kristian
    The glucose oxidation cascade is fascinating; although oxidation products have high economic value, they can manipulate the biological activity through posttranslational modification such as glycosylation of proteins, lipids, and nucleic acids. The concept of this work is based on the ability of reactive species induced by cold atmospheric plasma (CAP) in aqueous liquids and the corresponding gas-liquid interface to oxidize biomolecules under ambient conditions. Here, we report the oxidation of glucose by an argon-based dielectric barrier discharge plasma jet (kINPen) with a special emphasis on examining the reaction pathway to pinpoint the most prominent reactive species engaged in the observed oxidative transformation. Employing d-glucose and d-glucose-13C6solutions and high-resolution mass spectrometry and ESI-tandem MS/MS spectrometry techniques, the occurrence of glucose oxidation products, for example, aldonic acids and aldaric acids, glucono- and glucaro-lactones, as well as less abundant sugar acids including ribonic acid, arabinuronic acid, oxoadipic acid, 3-deoxy-ribose, glutaconic acid, and glucic acid were surveyed. The findings provide deep insights into CAP chemistry, reflecting a switch of reactive species generation with the feed gas modulation (Ar or Ar/O2with N2curtain gas). Depending on the gas phase composition, a combination of oxygen-derived short-lived hydroxyl (•OH)/atomic oxygen [O(3P)] radicals was found responsible for the glucose oxidation cascade. The results further illustrate that the presence of carbohydrates in cell culture media, gel formulations (agar), or other liquid targets (juices) modulate the availability of CAP-generated species in vitro. In addition, a glycocalyx is attached to many mammalian proteins, which is essential for the respective physiologic role. It might be questioned if its oxidation plays a role in CAP activity.