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  1. Article ; Online: Unusually cyclized triterpenoids: occurrence, biosynthesis and chemical synthesis.

    Hussain, Hidayat / Xiao, Jianbo / Ali, Akbar / Green, Ivan R / Westermann, Bernhard

    Natural product reports

    2023  Volume 40, Issue 2, Page(s) 412–451

    Abstract: Covering: 2009 to 2021Biosynthetically, most of the syntheses of triterpenes follow the cascade cyclization and rearrangement of the acyclic ... ...

    Abstract Covering: 2009 to 2021Biosynthetically, most of the syntheses of triterpenes follow the cascade cyclization and rearrangement of the acyclic precursors
    MeSH term(s) Triterpenes/chemistry ; Squalene/chemistry ; Cyclization
    Chemical Substances Triterpenes ; oxidosqualene (2Y5JJZ8E4W) ; Squalene (7QWM220FJH)
    Language English
    Publishing date 2023-02-22
    Publishing country England
    Document type Journal Article ; Review
    ZDB-ID 2002546-4
    ISSN 1460-4752 ; 0265-0568
    ISSN (online) 1460-4752
    ISSN 0265-0568
    DOI 10.1039/d2np00033d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Chemical Synthesis of

    Milde, Raika / Schnabel, Arianne / Ditfe, Toni / Hoehenwarter, Wolfgang / Proksch, Carsten / Westermann, Bernhard / Vogt, Thomas

    Molecules (Basel, Switzerland)

    2022  Volume 27, Issue 20

    Abstract: Capsaicin, produced by ... ...

    Abstract Capsaicin, produced by diverse
    MeSH term(s) Capsaicin/metabolism ; Escherichia coli/genetics ; Escherichia coli/metabolism ; Amino Acids, Branched-Chain ; Pharmaceutical Preparations ; Coenzyme A ; Bacterial Outer Membrane Proteins ; Escherichia coli Proteins
    Chemical Substances Capsaicin (S07O44R1ZM) ; Amino Acids, Branched-Chain ; Pharmaceutical Preparations ; Coenzyme A (SAA04E81UX) ; traN protein, E coli (147416-08-8) ; Bacterial Outer Membrane Proteins ; Escherichia coli Proteins
    Language English
    Publishing date 2022-10-13
    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/molecules27206878
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.MO 81: Show issues

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  3. Article ; Online: Multicomponent synthesis of α-acylamino and α-acyloxy amide derivatives of desmycosin and their activity against gram-negative bacteria.

    Budragchaa, Tuvshinjargal / Westermann, Bernhard / Wessjohann, Ludger A

    Bioorganic & medicinal chemistry

    2019  Volume 27, Issue 15, Page(s) 3237–3247

    Abstract: Bacterial resistance to the existing drugs requires constant development of new antibiotics. Developing compounds active against gram-negative bacteria thereby is one of the more challenging tasks. Among the many approaches to develop successful ... ...

    Abstract Bacterial resistance to the existing drugs requires constant development of new antibiotics. Developing compounds active against gram-negative bacteria thereby is one of the more challenging tasks. Among the many approaches to develop successful antibacterials, medicinal chemistry driven evolution of existing successful antibiotics is considered to be the most effective one. Towards this end, the C-20 aldehyde moiety of desmycosin was modified into α-acylamino and α-acyloxy amide functionalities using isonitrile-based Ugi and Passerini reactions, aiming for enhanced antibacterial and physicochemical properties. The desired compounds were obtained in 45-93% yield under mild conditions. The antibacterial activity of the resulting conjugates was tested against gram-negative Aliivibrio fischeri. The antibiotic strength is mostly governed by the amine component introduced. Thus, methylamine derived desmycosin bis-amide 4 displayed an enhanced inhibition rate vs. desmycosin (99% vs. 83% at 1 µM). Derivatives with long acyclic or bulky amine and isocyanide Ugi components reduced potency, whereas carboxylic acid reagents with longer chain length afforded increased bioactivity. In Passerini 3-component products, the butyric ester amide 22 displayed a higher activity (90% at 1 µM) than the parent compound desmycosin (2).
    MeSH term(s) Aliivibrio fischeri/drug effects ; Amides/chemical synthesis ; Amides/chemistry ; Amides/pharmacology ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Dose-Response Relationship, Drug ; Microbial Sensitivity Tests ; Molecular Structure ; Structure-Activity Relationship ; Tylosin/analogs & derivatives ; Tylosin/chemical synthesis ; Tylosin/chemistry ; Tylosin/pharmacology
    Chemical Substances Amides ; Anti-Bacterial Agents ; tylosin B (11032-98-7) ; Tylosin (YEF4JXN031)
    Language English
    Publishing date 2019-06-01
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1161284-8
    ISSN 1464-3391 ; 0968-0896
    ISSN (online) 1464-3391
    ISSN 0968-0896
    DOI 10.1016/j.bmc.2019.05.046
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 3815: 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: Cultural Characterization and Antagonistic Activity of Cladobotryum virescens against Some Phytopathogenic Fungi and Oomycetes

    Hernández, Giselle / Ramos, Beatriz / Sultani, Haider N. / Ortiz, Yarelis / Spengler, Iraida / Castañeda, Rafael F. / Rivera, Daniel G. / Arnold, Norbert / Westermann, Bernhard / Mirabal, Yaneris

    Agronomy. 2023 Jan. 28, v. 13, no. 2

    2023  

    Abstract: In this study, the characteristic growth of Cladobotryum virescens on nine culture media was analyzed. The growing behavior of this fungus was dependent on the culture medium. In vitro analysis showed that oat agar was better than other media tested with ...

    Abstract In this study, the characteristic growth of Cladobotryum virescens on nine culture media was analyzed. The growing behavior of this fungus was dependent on the culture medium. In vitro analysis showed that oat agar was better than other media tested with the highest conidia production. The antifungal activity against Fusarium chlamydosporum and Alternaria brassicicola was evaluated by the Dual Culture method. C. virescens displayed high activity against both pathogens acting through antibiosis and mycoparasitism. This effect was increased by a higher competitiveness of the strain for the substrate. Furthermore, the crude ethyl acetate extract of the culture broth was tested in vitro against Botrytis cinerea and Septoria tritici, as well as the hemibiotrophic oomycete Phytophthora infestans using a microtiter plate assay at different concentrations. The extract showed excellent inhibition even below 5 ppm. According to these results, we concluded that C. virescens can be considered as a potential biological control agent in agriculture. To the best of our knowledge, this is the first study to investigate C. virescens as a biocontrol agent for different diseases caused by five relevant pathogens that affect cereals and vegetables.
    Keywords Alternaria brassicicola ; Botrytis cinerea ; Fusarium chlamydosporum ; Hypomyces ; Mycosphaerella graminicola ; Phytophthora infestans ; agar ; agronomy ; antibiosis ; antifungal properties ; biological control agents ; conidia ; culture media ; ethyl acetate ; fungi ; mycoparasites ; oats
    Language English
    Dates of publication 2023-0128
    Publishing place Multidisciplinary Digital Publishing Institute
    Document type Article ; Online
    ZDB-ID 2607043-1
    ISSN 2073-4395
    ISSN 2073-4395
    DOI 10.3390/agronomy13020389
    Database NAL-Catalogue (AGRICOLA)

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  5. Article ; Online: Isonitriles: Versatile Handles for the Bioorthogonal Functionalization of Proteins.

    Méndez, Yanira / Vasco, Aldrin V / Humpierre, Ana R / Westermann, Bernhard

    ACS omega

    2020  Volume 5, Issue 40, Page(s) 25505–25510

    Abstract: The property of the isonitrile group to enable the simultaneous α-addition of a strong electrophile and a nucleophile has always attracted the attention of organic chemists. Its versatility is augmented when recognizing that its high structural ... ...

    Abstract The property of the isonitrile group to enable the simultaneous α-addition of a strong electrophile and a nucleophile has always attracted the attention of organic chemists. Its versatility is augmented when recognizing that its high structural compactness, the inertia to most of the naturally occurring functional groups, and relatively prolonged physiological and metabolical stability, convert it into the smallest bioorthogonal group. The discovery and optimization of the isonitrile-tetrazine [4+1] cycloaddition as an alternative tool for the development of ligation and decaging strategies and the recently reported reaction of isonitriles with chlorooximes bring new opportunities for the utilization of this functional group in biological systems. Although several approaches have been reported for the synthesis of isonitrile-modified carbohydrates and polysaccharides, its incorporation in proteins has been barely explored. Besides compiling the reported methods for the assembly of isonitrile-modified proteins, this Mini-Review aims at calling attention to the real potential of this modification for protein ligation, decaging, immobilization, imaging, and many other applications at a low structural and functional cost.
    Language English
    Publishing date 2020-10-02
    Publishing country United States
    Document type Journal Article ; Review
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.0c03728
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy.

    Ricardo, Manuel G / Schwark, Markus / Llanes, Dayma / Niedermeyer, Timo H J / Westermann, Bernhard

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 47, Page(s) 12032–12035

    Abstract: Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe ... ...

    Abstract Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe the total synthesis of this specialized metabolite. The complex, highly brominated 1,2'-biindole could be synthesized via a Somei-type Michael reaction as key step. The optimised sequence yielded the natural product in five steps with an overall yield of 29 %.
    MeSH term(s) Animals ; Bird Diseases ; Central Nervous System Diseases ; Eagles ; Myelin Sheath ; Neurotoxins/toxicity
    Chemical Substances Neurotoxins
    Language English
    Publishing date 2021-06-18
    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.202101848
    Database MEDical Literature Analysis and Retrieval System OnLINE

    Full text online

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  7. Article ; Online: Diversification of a Novel α-Galactosyl Ceramide Hotspot Boosts the Adjuvant Properties in Parenteral and Mucosal Vaccines.

    Méndez, Yanira / Vasco, Aldrin V / Ebensen, Thomas / Schulze, Kai / Yousefi, Mohammad / Davari, Mehdi D / Wessjohann, Ludger A / Guzmán, Carlos A / Rivera, Daniel G / Westermann, Bernhard

    Angewandte Chemie (International ed. in English)

    2023  Volume 63, Issue 1, Page(s) e202310983

    Abstract: The development of potent adjuvants is an important step for improving the performance of subunit vaccines. CD1d agonists, such as the prototypical α-galactosyl ceramide (α-GalCer), are of special interest due to their ability to activate iNKT cells and ... ...

    Abstract The development of potent adjuvants is an important step for improving the performance of subunit vaccines. CD1d agonists, such as the prototypical α-galactosyl ceramide (α-GalCer), are of special interest due to their ability to activate iNKT cells and trigger rapid dendritic cell maturation and B-cell activation. Herein, we introduce a novel derivatization hotspot at the α-GalCer skeleton, namely the N-substituent at the amide bond. The multicomponent diversification of this previously unexplored glycolipid chemotype space permitted the introduction of a variety of extra functionalities that can either potentiate the adjuvant properties or serve as handles for further conjugation to antigens toward the development of self-adjuvanting vaccines. This strategy led to the discovery of compounds eliciting enhanced antigen-specific T cell stimulation and a higher antibody response when delivered by either the parenteral or the mucosal route, as compared to a known potent CD1d agonist. Notably, various functionalized α-GalCer analogues showed a more potent adjuvant effect after intranasal immunization than a PEGylated α-GalCer analogue previously optimized for this purpose. Ultimately, this work could open multiple avenues of opportunity for the use of mucosal vaccines against microbial infections.
    MeSH term(s) Adjuvants, Immunologic/pharmacology ; Galactosylceramides/pharmacology ; Galactosylceramides/chemistry ; Natural Killer T-Cells ; Vaccines
    Chemical Substances alpha-galactosylceramide ; Adjuvants, Immunologic ; Galactosylceramides ; Vaccines
    Language English
    Publishing date 2023-11-29
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202310983
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Book ; Online: Synthese von C- und O-glycosidierten 1,3-Aminopropanolen und deren weitere Verwendung

    Westermann, Bernhard

    Schlussbericht zu FNR 173 ; im Rahmen der Fördermaßnahme "Niedermolekulare Kohlenhydrate als nachwachsende Rohstoffe in chemischen und biotechnologischen Anwendungen"

    2004  

    Title variant Schlussbericht zu FNR 173 ; C-glycosidierten
    Author's details Bernhard Westermann
    Language German
    Size Online-Ressource (10 S., 80,4 KB), graph. Darst.
    Publisher Technische Informationsbibliothek u. Universitätsbibliothek ; Leibniz-Inst. für Pflanzenbiochemie, Natur- und Wirkstoffsynthese
    Publishing place Hannover ; Halle
    Document type Book ; Online
    Note Förderkennzeichen BMVEL 22017300 ; Unterschiede zwischen dem gedruckten Dokument und der elektronischen Ressource können nicht ausgeschlossen werden
    Database Library catalogue of the German National Library of Science and Technology (TIB), Hannover

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  9. Article ; Online: Rare Glutamic Acid Methyl Ester Peptaibols from

    Lam, Yen T H / Ricardo, Manuel G / Rennert, Robert / Frolov, Andrej / Porzel, Andrea / Brandt, Wolfgang / Stark, Pauline / Westermann, Bernhard / Arnold, Norbert

    International journal of molecular sciences

    2021  Volume 22, Issue 23

    Abstract: Fungal species of ... ...

    Abstract Fungal species of genus
    MeSH term(s) Antifungal Agents/pharmacology ; Antineoplastic Agents/pharmacology ; Ascomycota/drug effects ; Botrytis/drug effects ; Esters/chemistry ; Glutamic Acid/chemistry ; Humans ; Hypocreales/physiology ; Neoplasms/drug therapy ; Neoplasms/pathology ; Peptaibols/chemistry ; Peptaibols/pharmacology ; Phytophthora infestans/drug effects ; Tumor Cells, Cultured
    Chemical Substances Antifungal Agents ; Antineoplastic Agents ; Esters ; Peptaibols ; peptaibolin ; Glutamic Acid (3KX376GY7L)
    Language English
    Publishing date 2021-11-24
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms222312718
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Access to New Cytotoxic Triterpene and Steroidal Acid-TEMPO Conjugates by Ugi Multicomponent-Reactions.

    Sultani, Haider N / Morgan, Ibrahim / Hussain, Hidayat / Roos, Andreas H / Haeri, Haleh H / Kaluđerović, Goran N / Hinderberger, Dariush / Westermann, Bernhard

    International journal of molecular sciences

    2021  Volume 22, Issue 13

    Abstract: Multicomponent reactions, especially the Ugi-four component reaction (U-4CR), provide powerful protocols to efficiently access compounds having potent biological and pharmacological effects. Thus, a diverse library of betulinic acid (BA), fusidic acid ( ... ...

    Abstract Multicomponent reactions, especially the Ugi-four component reaction (U-4CR), provide powerful protocols to efficiently access compounds having potent biological and pharmacological effects. Thus, a diverse library of betulinic acid (BA), fusidic acid (FA), cholic acid (CA) conjugates with TEMPO (nitroxide) have been prepared using this approach, which also makes them applicable in electron paramagnetic resonance (EPR) spectroscopy. Moreover, convertible amide modified spin-labelled fusidic acid derivatives were selected for post-Ugi modification utilizing a wide range of reaction conditions which kept the paramagnetic center intact. The nitroxide labelled betulinic acid analogue
    MeSH term(s) Antineoplastic Agents/pharmacology ; Apoptosis/drug effects ; Cell Line, Tumor/drug effects ; Cholic Acid/chemistry ; Cyclic N-Oxides/chemistry ; Electron Spin Resonance Spectroscopy/methods ; Fusidic Acid/chemistry ; Humans ; Neoplasms/drug therapy ; Pentacyclic Triterpenes/chemistry ; Small Molecule Libraries/chemical synthesis ; Spin Labels ; Steroids/pharmacology ; Triterpenes/pharmacology
    Chemical Substances Antineoplastic Agents ; Cyclic N-Oxides ; Pentacyclic Triterpenes ; Small Molecule Libraries ; Spin Labels ; Steroids ; Triterpenes ; betulinic acid (4G6A18707N) ; Fusidic Acid (59XE10C19C) ; Cholic Acid (G1JO7801AE) ; TEMPO (VQN7359ICQ)
    Language English
    Publishing date 2021-07-01
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms22137125
    Database MEDical Literature Analysis and Retrieval System OnLINE

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