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19F NMR Spectroscopy

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Jan Kihlberg – One of the best experts on this subject based on the ideXlab platform.

  • Use of 19F NMR Spectroscopy to screen chemical libraries for ligands that bind to proteins.
    Organic & biomolecular chemistry, 2004
    Co-Authors: Tobias Tengel, Tomas Fex, Hans Emtenäs, Fredrik Almqvist, Ingmar Sethson, Jan Kihlberg
    Abstract:

    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 19F 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 19F NMR spectrum. The results obtained for binding to PapD using 19F 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 19F NMR Spectroscopy should thus be a valuable addition to existing NMR techniques for evaluation of chemical libraries in bioorganic and medicinal chemistry.

  • Solid-Phase Synthesis of α-Gal Epitopes: On-Resin Analysis of Solid-Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
    The Journal of organic chemistry, 2003
    Co-Authors: Mickael Mogemark, Mikael Elofsson, Jan Kihlberg
    Abstract:

    A route for solid-phase synthesis of the α-Gal epitopes Gal(α1−3)Gal(β1−4)Glc and Gal(α1−3)Gal(β1−4)GlcNAc is described. These trisaccharide antigens are responsible for hyperacute rejection in xenotransplantation of porcine organs. Optimization of the solid-phase synthesis relied on use of fluorinated protective groups for the carbohydrate building blocks and use of a fluorinated linker. This allowed convenient on-resin analysis of the reactions with gel-phase 19F NMR Spectroscopy. Conditions were established which allowed reductive ring-opening of 4,6-O-benzylidene acetals to be performed on the solid phase with high regioselectivity to furnish the corresponding 6-O-benzyl ethers. It was found that glycosylations could be conveniently carried out by using thioglycosides as donors with N-iodosuccinimide and trifluoromethanesulfonic acid as the promoter system. With use of these conditions a challenging α-glycosidic linkage was successfully installed with complete stereoselectivity in the final glycosylat…

  • Fluorinated protective groups for on-resin quantification of solid-phase oligosaccharide synthesis with 19F NMR Spectroscopy.
    Chembiochem : a European journal of chemical biology, 2002
    Co-Authors: Mickael Mogemark, Mikael Elofsson, Jan Kihlberg
    Abstract:

    Fluorinated Protective Groups for On-Resin Quantification of Solid- Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy

Mikael Elofsson – One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and evaluation of 2-(2-fluoro-4-hydroxymethyl-5-methoxy-phenoxy)acetic acid as a linker in solid-phase synthesis monitored by gel-phase 19F NMR Spectroscopy
    Organic & biomolecular chemistry, 2007
    Co-Authors: Fredrik K. Wallner, Sara Spjut, Dan Boström, Mikael Elofsson
    Abstract:

    Gel-phase 19F NMR Spectroscopy is a useful monitoring technique for solid-phase organic chemistry due to the high information content it delivers and swift acquisition times, using standard NMR spectrometers. This paper describes the synthesis of the novel linker 2-(2-fluoro-4-hydroxymethyl-5-methoxy-phenoxy)acetic acid in 29% yield over seven steps, using nucleophilic aromatic substitutions on 2,4,5-trifluorobenzonitrile as key steps. Following standard solid-phase synthesis a peptide could be cleaved from the linker using 20% TFA in CH2Cl2 in 30 minutes, in contrast to a previously described monoalkoxy linker that requires 90% TFA in water at elevated temperature. A resin-bound peptide could be successfully glycosylated using only two equivalents of a thioglycoside donor, activated with N-iodosuccinimide and trifluoromethanesulfonic acid, and subsequent cleavage and deprotection gave the target glycopeptide. Direct glycosylation of the linker itself followed by mild acidic cleavage gave a fully protected hemiacetal for further chemical manipulation.

  • Solid-Phase Synthesis of α-Gal Epitopes: On-Resin Analysis of Solid-Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
    The Journal of organic chemistry, 2003
    Co-Authors: Mickael Mogemark, Mikael Elofsson, Jan Kihlberg
    Abstract:

    A route for solid-phase synthesis of the α-Gal epitopes Gal(α1−3)Gal(β1−4)Glc and Gal(α1−3)Gal(β1−4)GlcNAc is described. These trisaccharide antigens are responsible for hyperacute rejection in xenotransplantation of porcine organs. Optimization of the solid-phase synthesis relied on use of fluorinated protective groups for the carbohydrate building blocks and use of a fluorinated linker. This allowed convenient on-resin analysis of the reactions with gel-phase 19F NMR Spectroscopy. Conditions were established which allowed reductive ring-opening of 4,6-O-benzylidene acetals to be performed on the solid phase with high regioselectivity to furnish the corresponding 6-O-benzyl ethers. It was found that glycosylations could be conveniently carried out by using thioglycosides as donors with N-iodosuccinimide and trifluoromethanesulfonic acid as the promoter system. With use of these conditions a challenging α-glycosidic linkage was successfully installed with complete stereoselectivity in the final glycosylat…

  • Fluorinated protective groups for on-resin quantification of solid-phase oligosaccharide synthesis with 19F NMR Spectroscopy.
    Chembiochem : a European journal of chemical biology, 2002
    Co-Authors: Mickael Mogemark, Mikael Elofsson, Jan Kihlberg
    Abstract:

    Fluorinated Protective Groups for On-Resin Quantification of Solid- Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy

Mickael Mogemark – One of the best experts on this subject based on the ideXlab platform.

  • Solid-phase glycoconjugate synthesis : on-resin analysis with gel-phase ¹9F NMR Spectroscopy
    , 2005
    Co-Authors: Mickael Mogemark
    Abstract:

    An efficient and versatile non-destructive method to analyze the progress of solid-phase glycoconjugate synthesis with gel-phase 19F NMR Spectroscopy is described. The method relies on use of fluor …

  • Solid-Phase Synthesis of α-Gal Epitopes: On-Resin Analysis of Solid-Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
    The Journal of organic chemistry, 2003
    Co-Authors: Mickael Mogemark, Mikael Elofsson, Jan Kihlberg
    Abstract:

    A route for solid-phase synthesis of the α-Gal epitopes Gal(α1−3)Gal(β1−4)Glc and Gal(α1−3)Gal(β1−4)GlcNAc is described. These trisaccharide antigens are responsible for hyperacute rejection in xenotransplantation of porcine organs. Optimization of the solid-phase synthesis relied on use of fluorinated protective groups for the carbohydrate building blocks and use of a fluorinated linker. This allowed convenient on-resin analysis of the reactions with gel-phase 19F NMR Spectroscopy. Conditions were established which allowed reductive ring-opening of 4,6-O-benzylidene acetals to be performed on the solid phase with high regioselectivity to furnish the corresponding 6-O-benzyl ethers. It was found that glycosylations could be conveniently carried out by using thioglycosides as donors with N-iodosuccinimide and trifluoromethanesulfonic acid as the promoter system. With use of these conditions a challenging α-glycosidic linkage was successfully installed with complete stereoselectivity in the final glycosylat…

  • Fluorinated protective groups for on-resin quantification of solid-phase oligosaccharide synthesis with 19F NMR Spectroscopy.
    Chembiochem : a European journal of chemical biology, 2002
    Co-Authors: Mickael Mogemark, Mikael Elofsson, Jan Kihlberg
    Abstract:

    Fluorinated Protective Groups for On-Resin Quantification of Solid- Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy