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  • 1.
    Mogemark, Mickael
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Gårdmo, Frida
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Tengel, Tobias
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Kihlberg, Jan
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Elofsson, Mikael
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Gel-phase F-19 NMR spectral quality for resins commonly used in solid-phase organic synthesis: a study of peptide solid-phase glycosylations2004In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 2, p. 1770-1776Article in journal (Refereed)
    Abstract [en]

    The spectroscopic properties for seven different commercial resins used in solid-phase synthesis were investigated with F-19 NMR spectroscopy. A fluorine-labeled dipeptide was synthesized on each resin, and the resolution of the F-19 resonances in CDCl3, DMSO-d(6), benzene-d(6) and CD3OD were measured with a conventional NMR spectrometer, i.e. without using magic angle spinning. In general, resins containing poly(ethylene glycol) chains (ArgoGel, TentaGel and PEGA) were found to be favorable for the F-19 NMR spectral quality. Three serine containing tri-, penta-, and heptapeptides were then prepared on an ArgoGel resin functionalized with a fluorine-labeled linker. The resin bound peptides were glycosylated utilizing a thiogalactoside glycosyl donor carrying fluorine-labeled protective groups. Monitoring of the glycosylations with gel-phase F-19 NMR spectroscopy allowed each glycopeptide to be formed in similar to80% yield, using a minimal amount of glycosyl donor (3 x 2 equivalents). In addition, it was found that the glycosylation yields were independent of peptide length.

  • 2.
    Pudelko, Maciej
    et al.
    Umeå University, Faculty of Science and Technology, Chemistry.
    Lindgren, Anna
    Umeå University, Faculty of Science and Technology, Chemistry.
    Tengel, Tobias
    Umeå University, Faculty of Science and Technology, Chemistry.
    Reis, Celso A.
    Elofsson, Mikael
    Umeå University, Faculty of Science and Technology, Chemistry.
    Kihlberg, Jan
    Umeå University, Faculty of Science and Technology, Chemistry.
    Formation of lactones from sialylated MUC1 glycopeptides2006In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, no 4, p. 713-20Article in journal (Refereed)
    Abstract [en]

    The tumor-associated carbohydrate antigens TN, T, sialyl TN and sialyl T are expressed on mucins in several epithelial cancers. This has stimulated studies directed towards development of glycopeptide-based anticancer vaccines. Formation of intramolecular lactones involving sialic acid residues and suitably positioned hydroxyl groups in neighboring saccharide moieties is known to occur for glycolipids such as gangliosides. It has been suggested that these lactones are more immunogenic and tumor-specific than their native counterparts and that they might find use as cancer vaccines. We have now investigated if lactonization also occurs for the sialyl TN and T antigens of mucins. It was found that the model compound sialyl T benzyl glycoside , and the glycopeptide Ala-Pro-Asp-Thr-Arg-Pro-Ala from the tandem repeat of the mucin MUC1, in which Thr stands for the 2,3-sialyl-T antigen, lactonized during treatment with glacial acetic acid. Compound gave the 1''--> 2' lactone as the major product and the corresponding 1''--> 4' lactone as the minor product. For glycopeptide the 1''--> 4' lactone constitued the major product, whereas the 1''--> 2' lactone was the minor one. When lactonized was dissolved in water the 1''--> 4' lactone underwent slow hydrolysis, whereas the 1''--> 2' remained stable even after a 30 days incubation. In contrast the corresponding 2,6-sialyl-TN glycopeptide did not lactonize in glacial acetic acid.

  • 3.
    Tengel, Tobias
    et al.
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Alcocer, Marcos J C
    Schleucher, Jürgen
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Larsson, Göran
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Complete assignment and secondary structure of the Brazil nut allergen Ber e 1.2005In: Journal of Biomolecular NMR, ISSN 0925-2738, E-ISSN 1573-5001, Vol. 32, no 4, p. 336-Article in journal (Refereed)
  • 4.
    Tengel, Tobias
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Fex, Tomas
    Emtenäs, Hans
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Almqvist, Fredrik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Sethson, Ingmar
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Kihlberg, Jan
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Use of 19F NMR spectroscopy to screen chemical libraries for ligands that bind to proteins2004In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 2, no 5, p. 725-731Article in journal (Refereed)
    Abstract [en]

    Identification of compounds from chemical libraries that bind to macromolecules by use of NMR spectroscopy has gained increasing importance during recent years. A simple methodology based on F-19 NMR spectroscopy for the screening of ligands that bind to proteins, which also provides qualitative information about relative binding strengths and the presence of multiple binding sites, is presented here. A library of fluorinated compounds was assembled and investigated for binding to the two bacterial chaperones PapD and FimC, and also to human serum albumin (HSA). It was found that library members which are bound to a target protein could be identified directly from line broadening and/or induced chemical shifts in a single, one-dimensional F-19 NMR spectrum. The results obtained for binding to PapD using F-19 NMR spectroscopy agreed well with independent studies based on surface plasmon resonance, providing support for the versatility and accuracy of the technique. When the library was titrated to a solution of PapD chemical shift and linewidth changes were observed with increasing ligand concentration, which indicated the presence of several binding sites on PapD and enabled the assessment of relative binding strengths for the different ligands. Screening by F-19 NMR spectroscopy should thus be a valuable addition to existing NMR techniques for evaluation of chemical libraries in bioorganic and medicinal chemistry.

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