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  • 2601.
    Åslund, Andreas
    et al.
    Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry. Linköping University, The Institute of Technology.
    Nilsson, Peter
    Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry. Linköping University, The Institute of Technology.
    Konradsson, Peter
    Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry. Linköping University, The Institute of Technology.
    Synthesis of a pentathiophene fluorescent probe, 4’,3’’’-Bis-carboxymethyl-[2,2’;5’,2’’;5’’,2’’’;5’’’,2’’’‘]quinquethiophene-5,5’2010In: Nature Protocols, ISSN 1754-2189Article in journal (Other academic)
    Abstract [en]

    Poly and oligo-thiophenes have previously been used for in vitro, ex vivo and in vivo imaging of protein aggregates. The probe (p-FTAA) has been developed for the purpose of in vivo staining of protein aggregates such as amyloid deposits. It effectively passes the blood brain barrier and imaging can be performed live with two-photon imaging or ex vivo.

    The straightforward synthesis of p-FTAA, including two Suzuki couplings, makes it an attractive probe for studies of most diseases involving protein aggregates.

  • 2602.
    Öhberg, Liselotte
    Stockholm University.
    Synthesis of a key derivative of glycosylphosphatidylinositol substances and synthesis of spacer glycosides for use in the formation of glycoconjugates and of self-assembled monolayer surfaces1998Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first chapter of this thesis describes glycosylation strategies for obtaining derivatives of 2-amino-2-deoxy-a-D-glucopyranosyl-(1-->6)-D-myo-inositol, a key building block for synthesis of glycosylphosphatidylinositol anchor substances and also proposed to be part of a second messenger for insulin.

    The second chapter describes the synthesis of bifunctional oligoethylene glycol spacers and glycosylation of these for use in formation of glycoconjugates. Synthesis of glycosyl succinimides and their conversion into glycoconjugates are also described.

    In the third chapter, synthesis of various terminated alkane thiols are described for use in formation of self-assembled monolayer surfaces. Globotriose linked alkane thiols with or without oligoethylene glycol spacers in between were mixed with hydroxyl or oligoethylene glycol terminated alkane thiols for formation of model surfaces.

  • 2603.
    Öhrngren, Per
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Fardost, Ashkan
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Russo, Francesco
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Fagrell, Magnus
    WaveCraft AB.
    Schanche, Jon-Sverre
    WaveCraft AB.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Evaluation of a Nonresonant Microwave Applicator for Continuous-Flow Chemistry Applications2012In: Organic Process Research & Development, ISSN 1083-6160, E-ISSN 1520-586X, Vol. 16, no 5, p. 1053-1063Article in journal (Refereed)
    Abstract [en]

    The concept of a nonresonant microwave applicator for continuous-flow organic chemistry is introduced and evaluated. The frequency of the incident microwave radiation can be adjusted between 2.4 and 2.5 GHz to optimize the energy absorbance. The temperature of the reaction is monitored by five IR sensors, and their signals can be used to automatically adjust the power output from the microwave generator. The heating of several different solvents up to 20 degrees C above the standard boiling point has been explored. Several different organic reactions have been successfully carried out using a 200 mm X (sic) 3 mm tubular borosilicate reactor and a flow between 47 and 2120 mu L/min. The microwave heating pattern was visualized with an IR camera. The transformations include palladium-catalyzed coupling reactions (oxidative Heck and Suzuki reactions), heterocyclic chemistry (oxathiazolone and Fischer indole synthesis), rearrangement (Claisen), and a Diels-Alder cycloaddition reaction. A scale-out to 57 mmol/h was performed with the Fischer indole reaction.

  • 2604. Öksnes Dalheim, Marianne
    et al.
    Björk Arnfinnsdottir, Nina
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Christensen, Björn E.
    The size and shape of three water-soluble, non-ionic polysaccharides produced by lactic acid bacteria: A comparative study2016In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 142, p. 91-97Article in journal (Refereed)
    Abstract [en]

    Three water-soluble, non-ionic extracellular polysaccharides (EPS) obtained from lactic acid bacteria (S. thermophilus THS, L. helveticus K16 and S. thermophilus ST1) were subjected to a comparative study by means of multidetector size-exclusion chromatography, providing distributions and averages of molar masses, radii of gyration and intrinsic viscosities. All polysaccharides displayed random coil character. Further analysis of the data reveals differences in chain stiffness and extension that could be well correlated to structural features. The calculated persistence lengths ranged from 5 to 10 nm and fall within the range typical for many single-stranded bacterial or plant polysaccharides. The ST1 polysaccharide had the highest molar mass but the lowest persistence length, which is attributed to the presence of the flexible (1 6)-linkage in the main chain.

  • 2605.
    Östervall, Jennie
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Conformational Dynamics of Carbohydrates Studied by NMR Spectroscopy and Molecular Simulations2006Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Carbohydrates play important roles in biological processes. Their function is closely related to their conformation. In this thesis, conformational studies of carbohydrates by NMR spectroscopy and molecular dynamics computer simulations are described.

    The first two papers discuss the anomalous solubility of β-cyclodextrin compared to other cyclodextrins. Time correlation functions revealed flexibility in all cyclodextrins. Molecular dynamics computer simulations showed that the glycosidic linkages were rather rigid and the flexibility was suggested to be macrocyclic. From spatial distribution functions β-cyclodextrin was found to have greater ability to order the surrounding water than the other cyclodextrins. Paper III deals with some of the difficulties of conformational studies. In Paper IV, a new method, Additative Potential Maximum Entropy, APME, is applied to a disaccharide. Conformational distribution functions are derived from NOEs, J-couplings and residual dipolar couplings and calculated from computer simulations. All distribution functions were found to be in good agreement. In papers V and VI oligosaccharides from human milk are studied. Residual dipolar coupling, J-couplings and cross relaxation rates were measured by NMR spectroscopy and molecular dynamics computer simulations were carried out. Both oligosaccharides showed high flexibility for the β-D-GlcpNAc-(1→3)-β-D-Galp linkage.

  • 2606.
    Öyaas, K.
    et al.
    RISE, Innventia, PFI – Paper and Fiber Research Institute.
    Johnsen, I.A.
    Hoff, B.H.
    Opedal, M.T.
    Toven, K.
    RISE, Innventia, PFI – Paper and Fiber Research Institute.
    Gulbrandsen, T.Aa.
    Hot water extraction of hemicellulose from softwood and sugarcane bagasse using microwave heating technology2012Conference paper (Refereed)
  • 2607. Číhalová, Sylva
    et al.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Veselý, Jan
    Asymmetric Aza-Morita–Baylis–Hillman-type reactions: The highly enantioselective reaction between unmodified α,β-unsaturated aldehydes and N-acylimines by organo-co-catal2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 7, p. 1096-1108Article in journal (Refereed)
    Abstract [en]

    The highly enantioselective organo-co-catalytic aza-Morita–Baylis–Hillman (MBH)-type reaction between N-carbamate-protected imines and α,β-unsaturated aldehydes has been developed. The organic co-catalytic system of proline and 1,4-diazabicyclo[2.2.2]octane (DABCO) enables the asymmetric synthesis of the corresponding N-Boc- and N-Cbz-protected β-amino-α-alkylidene-aldehydes in good to high yields and up to 99% ee. In the case of aza-MBH-type addition of enals to phenylprop-2-ene-1-imines, the co-catalytic reaction exhibits excellent 1,2-selectivity. The organo-co-catalytic aza-MBH-type reaction can also be performed by the direct highly enantioselective addition of α,β-unsaturated aldehydes to bench-stableN-carbamate-protected α-amidosulfones to give the corresponding β-amino-α-alkylidene-aldehydes with up to 99% ee.The organo-co-catalytic aza-MBH-type reaction is also an expeditious entry to nearly enantiomerically pure β-amino-α-alkylidene-amino acids and β-amino-α-alkylidene-lactams (99% ee). The mechanism and stereochemistry of the chiral amine and DABCO co-catalyzed aza-MBH-type reaction arealso discussed.

  • 2608.
    Ślósarczyk, Adam T.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Peptide Conjugates as Useful Molecular Tools2011Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The conjugation of a small organic molecule to synthetic polypeptides from a designed set has been shown to give rise to binders with high affinity and selectivity for the phosphorylated model proteins α-casein and β-casein but not for ovoalbumin. The small organic molecule that was used for this purpose is comprised of two di-(2-picolyl)amine groups assembled on a dimethylphenyl scaffold, and is capable of complexing two Zn2+ ions to form chelates that bind the phosphate ion. The designed polypeptides used for binder construction have no precedence in nature and do not show any prior selectivity favouring any single protein. The polypeptide conjugate binders showed high affinity towards the model protein α-casein, the binder molecule 4C15L8-PP1 bound α-casein with a dissociation constant KD of 17 nM, although the di-(2-picolyl) amine based chelate in the presence of Zn2+ bound phosphate ion with dissociation constants in the low mM range. The observed affinity is due to interactions between the Zn2+ chelate and the phosphate groups of α-casein and also to interactions between the polypeptide scaffold and α-casein. The binder was found to selectively extract α-casein from buffer, bovine milk and human serum spiked with α-casein. The flexible construction of the binder permits for flexible modifications like attachment of fluorophores for titrations and quantifications. The binders were shown to efficiently capture α-casein from human serum when immobilized on solid support in a continuous flow system and to release the captured α-casein upon a simple change of pH using 0.1% acqueous trifluoroacetica acid. The developed technology brings new opportunities in investigating posttranslational phosphorylation events that are involved in signaling cascades and triggering many biologically relevant functions.

    A new chemical linker technology has also been developed for the purpose of conjugating biomolecules taking advantage of amino groups for the conjugation. By combining two esters with different reactivities, separated by an aliphatic chain, a molecular tool was developed that allows for controlled conjugation of biomolecules. The two esters react at different rates and can therefore be separated and allowed to react under different conditions in each step, thereby allowing for selective linkage formation between the subunits. The size of the spacer can be varied by selecting the appropriate dicarboxylic acid. The developed technology was shown to provide specificity in heteroconjugate formation in the assembly of a variety of heteroconjugates where polypeptides were combined with other peptides, carbohydrates and proteins.

  • 2609.
    Chow, Shiao Y. (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Stevens, Marc Y. (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Åkerbladh, Linda (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Bergman, Sara (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Odell, Luke R. (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 27, p. 9037-9037Article in journal (Other academic)
    Abstract [en]

    Invited for the cover of this issue is the group of L. R. Odell at Uppsala University (Sweden). The image depicts iridium at the center of a vortex of electrons that are transferred to and from the surrounding reaction components in aradical aminocarbonylation method. Read the full text of the article at 10.1002/chem.201601694.

  • 2610.
    Chow, Shiao Y. (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Stevens, Marc Y. (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Åkerbladh, Linda (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Bergman, Sara (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Odell, Luke R. (Contributor)
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 27, p. 9033-Article in journal (Other academic)
    Abstract [en]

    Iridium stands at the center of a vortex of electrons that are transferred to and from the surrounding reaction components in this radical aminocarbonylation method. The combination of visible-light irradiation and low-pressure ex situ carbon monoxide generation makes this an attractive and operationally simple approach for preparing β-hydride-containing alkyl amides. Additional cover art acknowledgements: Bobo Skillinghaug and Johan Sjöstedt. More information can be found in the Full Paper by L. R. Odell et al. on page 9155 ff.

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