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  • 1.
    Behren, Sandra
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Westerlind, Ulrika
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Novel approaches to design glycan-based antibacterial inhibitors2023In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 26, no 1, article id e202200795Article, review/survey (Refereed)
    Abstract [en]

    The interactions between bacterial lectins and carbohydrates on the host cell surface can mediate bacterial adhesion, invasion, and immune evasion. Multivalency plays a key role in these binding events. However, additional molecular mechanisms greatly impact multivalent binding recognition. To develop specific and effective bacterial inhibitors, a deeper understanding of the complex underlying mechanisms of bacterial adhesion processes is necessary. By interfering with bacterial adhesion, synthetic multivalent glycoconjugates do not only have the potential to improve or replace antibiotic treatments, but also represent useful tools to study carbohydrate-pathogen interactions. In this review, we highlight a few recent advances in the synthesis and application of synthetic glycan-based scaffolds to uncover the nature of glycan-bacteria interactions and to design efficient bacterial inhibitors.

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  • 2.
    Chorell, Erik
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Chorell, Elin
    Umeå University, Faculty of Medicine, Department of Public Health and Clinical Medicine, Medicine.
    Efficient Synthesis of 2-Substituted Phthalimides from Phthalic Acids in One Step2013In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2013, no 33, p. 7512-7516Article in journal (Refereed)
    Abstract [en]

    Efficient procedures for synthesizing 2-substituted phthalimide (isoindole-1,3-dione) analogues starting from phthalic acids have been developed by using experimental design. The phthalimide central fragment frequently appears in biologically active compounds, materials, catalysts, and fluorescent probes, and therefore the development of general, fast, and convenient synthetic methods to this scaffold under neutral, acidic, and basic conditions would be attractive. After an initial screening, the use of acetonitrile, acetic acid, or pyridine in combination with microwave heating proved most promising. Experimental design was applied to these conditions to optimize the time, temperature, and concentration. This strategy has successfully generated synthetic methods that have been used to synthesize a series of phthalimides from phthalic acids and various amines or anilines in excellent yields. The developed methods have proven to be general, fast, convenient, and economic, and thus are expected to have broad utility to efficiently construct novel compounds for future biological and chemical applications.

  • 3.
    Kindahl, Tomas
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Chorell, Elin
    Umeå University, Faculty of Medicine, Department of Public Health and Clinical Medicine, Medicine.
    Chorell, Erik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Development and optimization of simple one-step methods for the synthesis of 4-amino-substituted 1,8-naphthalimides2014In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 28, p. 6175-6182Article in journal (Refereed)
    Abstract [en]

    The 1,8-naphthalimide central fragment can be found in a vast number of bioactive compounds and drugs in clinical trials, and can be recognized from their use as fluorescent probes. Of key importance for the fluorescent properties of the scaffold is the 4-amino substituent, which has also proven to be critical in several other chemical and biological applications. Because of the great interest in 1,8-naphthalimides in general, and 4-amino-substituted 1,8-naphthalimides in particular, we have developed and optimized one-step procedures with which to access these derivatives by using an experimental design approach. The multivariate studies of temperature, reaction time, and equivalents of substrates identified conditions with close to quantitative yields that could be applied to generate a range of 4-amino-substituted 1,8-naphthalimides in high yields.

  • 4.
    Lindgren, Anders E. G.
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Oberg, Christopher T.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Hillgren, J. Mikael
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Elofsson, Mikael
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Total Synthesis of the Resveratrol Oligomers (+/-)-Ampelopsin B and (+/-)-E-Viniferin2016In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 3, p. 426-429Article in journal (Refereed)
    Abstract [en]

    The total synthesis of the resveratrol dimers (+/-)-ampelopsin B and (+/-)-E-viniferin is reported. Highlights of the approach include the use of cyclopropylmethyl groups to protect aromatic alcohols. This group allows an acid promoted three-step, one-pot deprotection-epimerization-cyclization of an advanced intermediate to give (+/-)-ampelopsin B. An important advantage with our strategy is the possibility of synthesizing analogs to these natural products to further study the chemistry and biology of resveratrol oligomers.

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  • 5.
    Sellstedt, Magnus
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Dang, Hung The
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Prasad, G. Krishna
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Sauer, Uwe
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Almqvist, Fredrik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Four-Component Assembly of Natural-Product-Like Ring-Fused Isoquinuclidines2013In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2013, no 33, p. 7476-7479Article in journal (Refereed)
    Abstract [en]

    A four-component reaction between formyl-substituted 2-pyridones, aldehydes, amines, and activated alkenes has been developed. The resulting products are ring-fused natural-product-like isoquinuclidines. Three carbon–carbon bonds, two carbon–nitrogen bonds, and four or five stereocentres are formed in the reaction with overall product yields in the range 23–67 %. In most cases a single diastereomer was obtained. An intramolecular version of the reaction yielded analogues of the multi-ring-fused natural product catharanthine in a single step.

  • 6.
    Sellstedt, Magnus
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Nyberg, Anders
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Rosenbaum, Erik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Engström, Patrik
    Umeå University, Faculty of Medicine, Department of Molecular Biology (Faculty of Medicine). Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    Wickström, Malin
    Department of Medicinal Sciences, Division of Clinical Pharmacology, Uppsala University Hospital, 75185 Uppsala, Sweden.
    Gullbo, Joachim
    Department of Medicinal Sciences, Division of Clinical Pharmacology, Uppsala University Hospital, 75185 Uppsala, Sweden.
    Bergström, Sven
    Umeå University, Faculty of Medicine, Department of Molecular Biology (Faculty of Medicine). Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS). Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR).
    Johansson, Lennart B-Å
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Almqvist, Fredrik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Synthesis and characterization of a multi ring-fused 2-pyridone-based fluorescent scaffold2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 32, p. 6171-6178Article in journal (Refereed)
    Abstract [en]

    A series of compounds based on a novel fluorescent scaffold have been synthesized. Most of the compounds displayed high quantum yields of fluorescence and unusually long fluorescence lifetimes. HeLa cells were treated with one of the compounds and its use as a fluorescent dye was demonstrated with fluorescence confocal microscopy.

  • 7.
    Spjut, Sara
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Pudelko, Maciej
    Institut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
    Hartmann, Mirja
    Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel,Otto-Hahn-Platz 4, 24098 Kiel, Germany.
    Elofsson, Mikael
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Carbamate linker strategy in solid-phase synthesis of amino-functionalized glycoconjugates for attachment to solid surfaces and investigation of protein-carbohydrate interactions2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 3, p. 349-57Article in journal (Refereed)
    Abstract [en]

    Amino-functionalized serine-based galactose and glucose neoglycolipids were prepared by solid-phase synthesis using a carbamate strategy for anchoring amino functionalities to a (2-fluoro-4-hydroxymethylphenoxy)acetic acid linker resin. Key synthetic steps were monitored with gel-phase 19F NMR spectroscopy. Cleavage from the solid support was performed with trifluoroacetic acid. The terminal amine of the neoglycolipids was conjugated with didecyl squarate and then immobilized in amino-functionalized microtiter plates and the glycoconjugates were successfully probed with a galactose-binding lectin.

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