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  • 1. Pandey, Sunil Kumar
    et al.
    Guttormsen, Yngve
    Haug, Bengt Erik
    Hedberg, Christian
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Bayer, Annette
    A Concise Total Synthesis of Breitfussin A and B2015In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 1, p. 122-125Article in journal (Refereed)
    Abstract [en]

    The first total synthesis of breitfussin A and B is described. The approach features two palladium-catalyzed cross-couplings installing the indole and pyrrole onto the oxazole core and selective lithiation/iodination of a common indole-oxazole fragment providing 2,4-diiodinated or 2-iodinated oxazoles as potential precursors for breitfussin A and B, respectively. An unexpected acid promoted deiodination was utilized in the synthesis of breitfussin B. Comparison of the synthetic material with previously reported spectral data of isolated breitfussin A and B verified the structure of the breitfussin framework.

  • 2. Paulsen, Marianne H.
    et al.
    Karlsen, Eskil Andre
    Ausbacher, Dominik
    Anderssen, Trude
    Bayer, Annette
    Ochtrop, Philipp
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Hedberg, Christian
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Haug, Tor
    Sollid, Johanna U. Ericson
    Strøm, Morten B.
    An amphipathic cyclic tetrapeptide scaffold containing halogenated β2,2-amino acids with activity against multiresistant bacteria2018In: Journal of Peptide Science, ISSN 1075-2617, E-ISSN 1099-1387, Vol. 24, no 10, article id UNSP e3117Article in journal (Refereed)
    Abstract [en]

    The present study describes the synthesis and biological studies of a small series of head-to-tail cyclic tetrapeptides of the general structure c(Lys‐β2,2‐Xaa‐Lys) containing one lipophilic β2,2-amino acid and Lys, Gly, Ala, or Phe as the Xaa residue in the sequence. The peptides were investigated for antimicrobial activity against gram-positive and gram-negative reference strains and 30 multiresistant clinical isolates including strains with extended spectrum β-lactamase-carbapenemase (ESBL-CARBA) production. Toxicity was determined against human red blood cells. The most potent peptides showed high activity against the gram-positive clinical isolates with minimum inhibitory concentrations of 4-8μg/mL and low haemolytic activity. The combination of high antimicrobial activity and low toxicity shows that these cyclic tetrapeptides containing lipophilic β2,2-amino acids form a valuable scaffold for designing novel antimicrobial agents.

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