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  • 101.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Can template-template self-association contribute to polymer-ligand recognition characteristics?2000Conference paper (Refereed)
  • 102.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Koch-Schmidt, Ann-Christin
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ohlson, Sten
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Study of the Nature of Recognition in Molecularly Imprinted Polymers1996In: J. Mol. Recogn., Vol. 9, p 675-682Article in journal (Refereed)
  • 103.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Molecular Imprinting. Recent innovations in synthetic polymer receptor and enzyme mimics1997In: Recent Research Developments in Pure and Applied Chemistry, Vol. 1, p. 133-157Article in journal (Refereed)
  • 104.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Spectroscopic evaluation of molecular imprinting polymerization systems1997In: Bioorganic Chemistry, Vol. 25, p. 203-211Article in journal (Refereed)
  • 105.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    The development of molecular imprinting2000Other (Other academic)
  • 106.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Piletsky, S A
    Mosbach, K
    Koch-Schmidt, Ann-Christin
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Novel recognition elements for improved molecularly imprinted polymer stereoselectivity1997Conference paper (Refereed)
  • 107.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ramström, O
    Crown Ethers as a Tool for the Preparation of Molecularly Imprinted Polymers1998In: Journal of Molecular Recognition, Vol. 11, p. 103-106Article in journal (Refereed)
  • 108.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ramström, Olof
    Lund University.
    Crown ethers as a tool for the preparation of molecularly imprinted polymers1997Conference paper (Other academic)
  • 109.
    Andersson, Ida E.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Modified Glycopeptides Targeting Rheumatoid Arthritis: Exploring molecular interactions in class II MHC/glycopeptide/T-cell receptor complexes2011Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Rheumatoid arthritis (RA) is an autoimmune inflammatory disease that leads to degradation of cartilage and bone mainly in peripheral joints. In collagen-induced arthritis (CIA), a mouse model for RA, activation of autoimmune CD4+ T cells depends on a molecular recognition system where T-cell receptors (TCRs) recognize a complex between the class II MHC Aq protein and CII259-273, a glycopeptide epitope from type II collagen (CII). Interestingly, vaccination with the Aq/CII259-273 complex can relieve symptoms and cause disease regression in mice. This thesis describes the use of modified glycopeptides to explore interactions important for binding to the Aq protein and recognition by autoimmune T-cell hybridomas obtained from mice with CIA.

    The CII259-273 glycopeptide was modified by replacement of backbone amides with different amide bond isosteres, as well as substitution of two residues that anchor the glycopeptide in prominent pockets in the Aq binding site. A three-dimensional structure of the Aq/glycopeptide complex was modeled to provide a structural basis for interpretation of the modified glycopeptide’s immunological activities. Overall, it was found that the amide bond isosteres affected Aq binding more than could be explained by the static model of the Aq/glycopeptide complex. Molecular dynamics (MD) simulations, however, revealed that the introduced amide bond isosteres substantially altered the hydrogen-bonding network formed between the N-terminal 259-265 backbone sequence of CII259-273 and Aq. These results indicated that the N-terminal hydrogen-bonding interactions follow a cooperative model, where the strength and presence of individual hydrogen bonds depended on the neighboring interactions.

    The two important anchor residues Ile260 and Phe263 were investigated using a designed library of CII259-273 based glycopeptides with substitutions by different (non-)natural amino acids at positions 260 and 263. Evaluation of binding to the Aq protein showed that there was scope for improvement in position 263 while Ile was preferred in position 260. The obtained SAR understanding provided a valuable basis for future development of modified glycopeptides with improved Aq binding. Furthermore, the modified glycopeptides elicited varying T-cell responses that generally could be correlated to their ability to bind to Aq. However, in several cases, there was a lack of correlation between Aq binding and T-cell recognition, which indicated that the interactions with the TCRs were determined by other factors, such as presentation of altered epitopes and changes in the kinetics of the TCR’s interaction with the Aq/glycopeptide complex.

    Several of the modified glycopeptides were also found to bind well to the human RA-associated DR4 protein and elicit strong responses with T-cell hybridomas obtained from transgenic mice expressing DR4 and the human CD4 co-receptor. This encourages future investigations of modified glycopeptides that can be used to further probe the MHC/glycopeptide/TCR recognition system and that also constitute potential therapeutic vaccines for treatment of RA. As a step towards this goal, three modified glycopeptides presented in this thesis have been identified as candidates for vaccination studies using the CIA mouse model.

  • 110. Andersson, L I
    et al.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Mosbach, K
    Immunoassays using molecularly imprinted polymers1995In: Immunoanalysis of agrochemicals: emerging technologies / [ed] Judd O. Nelson, Alexander E. Karu and Rosie B. Wong, American Chemical Society (ACS), 1995, p. 89-97Conference paper (Other academic)
  • 111.
    Andersson, Linnéa
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry. Oorganisk kemi.
    Exploring expandable microspheres as a novel pore former in gel-cast macroporous alumina2008Licentiate thesis, monograph (Other academic)
    Abstract [en]

    Expandable microspheres have been explored as sacrificial templates for the production of macroporous ceramics. Concentrated alumina powder suspensions that contain expandable microspheres have been consolidated by gel-casting. The temperature range for the setting of the monomers and cross-linkers in the gel-casting system was tailored to allow the gas-filled polymer spheres to expand before the surrounding powder body became rigid. It has been demonstrated that it is possible to tune and tailor the porosity up to 86 % and the pore size distribution from 15 up to 150 micrometers by controlling the amount and size of the expandable microspheres. Scanning electron microscopy showed that the porosity became more and more open as the total porosity increased. This was corroborated by a preliminary study by X-ray µ Computed Tomography, which showed a very high connectivity between the pores, in a macroporous alumina body with a high porosity. The connectivity was reduced when alumina particles were deposited as a homogenous coating of on the expandable microspheres by a layer-by-layer coating process. The expandable microspheres has the advantage that a relatively low amount of organic material results in a large pore volume, which allow rapid and facile burn-out. It was demonstrated that the temperature induced expansion of the microspheres, and the associated increase of the suspension volume could be used as a novel casting method to yield macroporous alumina bodies with complex shapes. Ceramics produced with this method could find application ranging from bone scaffolds to low mass kiln furniture.

  • 112.
    Andersson, M.
    et al.
    YKI Institute for Surface Chemistry, Box 5607, SE-114 86 Stockholm, Sweden.
    Hillerström, A.
    YKI Institute for Surface Chemistry, Box 5607, SE-114 86 Stockholm, Sweden.
    Svensk, A.
    YKI Institute for Surface Chemistry, Box 5607, SE-114 86 Stockholm, Sweden.
    Younesi, S. R.
    YKI Institute for Surface Chemistry, Box 5607, SE-114 86 Stockholm, Sweden.
    Sjöström, E.
    Blute, I.
    Kjellin, M.
    Kizilng, J.
    Kronberg, B.
    Oldgren, J.
    Hansson, A.
    Sjöstrand, S.
    A New Class of Labile Surfactants that Break Down to Non-surface Active Products upon Heating or after a Pre-set Time, without the Need for a pH Change2007In: Tenside Surfactants Detergents, ISSN 0932-3414, E-ISSN 2195-8564, Vol. 44, no 6, p. 366-372Article in journal (Refereed)
    Abstract [en]

    A new class of labile surfactants that break down at a controllable rate without the need for a change in pH will be presented. The invention has been patented by YKI Institute for Surface Chemistry, and is based on use of β-keto acids or their salts as surface-active compounds. These surfactants spontaneously break down through decarboxylation, to form an oil-like ketone and CO 2/HCO 3 -/CO 32 - depending on pH. The rate of breakdown can be controlled within a wide range by temperature or by certain additives, but, unlike most cleavable surfactants, a change in pH is not needed. Furthermore the surfactants can be conveniently activated from a stabile precursor just before use, and one (of many possible) precursors of this kind is already available on the industrial scale in the form of a wellknown chemical that is FDA-approved in other, non-surfactant, applications. The compound in question, alkyl ketene dimer (AKD), is produced in large scale by a number of large chemical producers today, and used for hydrophobization of paper. The present article gives an overview of the surfactant chemistry, with focus on recent studies of the kinetics of activation of the surfactant precursor and breakdown kinetics of the labile surfactant at different conditions. Furthermore, possible industrial applications of the surfactant will be discussed, with one example taken from a recent feasibility study performed within the car washing area. © Carl Hanser Publisher.

  • 113.
    Andersson, Mats
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Determination of the structures of three bacterial polysaccharides and synthesis and use of new spacers for glycoconjugate formation1993Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first part of this work describes studies on the structures of three bacterial polysaccharides, i.e., the extracellular polysaccharides of Streptococcus pneumoniae type 2 and Butyrivibrio fibrisolvens strain X6C61 and the O-antigenic side-chain of the lipopolysaccharide of Escherichia coli 086.

    The second part describes the synthesis of new spacer molecules for oligosaccharide immobilization and their use in glycoconjugate formation.

  • 114.
    Andersson, Nina
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Mesostructured materials: Synthesis towards applications2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    A new class of materials with well-defined structures on mesoscopic (2-50 nm) length scales has attracted considerable interest during the last decade. These mesostructured mataterials are formed from the self-assembly of amphiphillic molecules and inorganic precursors. The aim of this thesis has been to develop preparation methods that are scalable, and at the same time allow for efficient structural control coupled with possibility to incorporate different functionalities.

    Two different industrial processes for production of particles with spherical morphology were successfully tailored for synthesis of well-ordered mesostructured particles. An existing spray drying method for a fast and continuous production was further developed, and for the first time, an emulsion-based method was implemented. The latter method resulted in superior control of both particle size and internal mesostructure.

    Mesostructured photochromic pigments were synthesised by incorporating photochromic dyes in the organic domains of the surfactant templated inorganic/organic mesostructured silica particles. The pigments were produced using a one-pot synthesis method employing an aerosol reactor, allowing control over both the internal mesostructure and the dye content. We show that transparent photochromic films can be prepared using latex binders and conventional coating technology.

    Mesoporous magnetic carrier materials were prepared by adding iron oxide nanoparticles during either the emulsion- or aerosol processing. The surfactant templated silica matrix displayed well-ordered internal pore architecture with limited pore blocking caused by the incorporated iron oxide nanoparticles. The iron oxide content was precisely controlled, and the magnetic properties were preserved during the processing. Finally we demonstrate that these materials can be used to magnetically separate water-soluble dyes from solution.

  • 115.
    Andersson, P.G.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Development of New Methodology for th Preparation of Optically Active Alcohols2004In: Pure Appl. Chem., no 76, p. 547-Article in journal (Refereed)
  • 116.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Development of a new methodology for the preparation of optically active alcohols*2004In: Pure Appl. Chem., Vol. 76, no 3, p. 547-555Article in journal (Refereed)
  • 117.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    On the Stereochemical Outcome of the McMurry Coupling of Acetophenone. A Reinvestigation1994In: Tetrahedron Letters, Vol. 35, no 16, p. 2609-2610Article in journal (Refereed)
  • 118.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Regio- and Stereoselective Deuteration of Allylic Chlorides Controlled by Neighboring Alcohol or Ether Groups1996In: J. Org. Chem., no 61, p. 4154-4156Article in journal (Refereed)
  • 119.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Aranyos, Attila
    Palladium-Mediated Stereo- and Regioselective Tandem-Cyclization-Carbonylations of 1,3-dienes1994In: Tetrahedron Letters, Vol. 35, no 25, p. 4441-4444Article in journal (Refereed)
  • 120.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bäckvall, Jan-E.
    Palladium-Catalyzed Tandem Cyclization of 4,6- and 5,7-Diene Amides. A New Route towards the Pyrrolizidine and Indolizidine Alkaloids1992In: J. Am. Chem. Soc., Vol. 114, no 22, p. 8696-8698Article in journal (Refereed)
  • 121.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bäckvall, Jan-E.
    Synthesis of Furanoid Terpenes via an Efficient Palladium-Catalyzed Cyclization of 4,6-Dienols1991In: J. Org. Chem., Vol. 56, no 18, p. 5349-5353Article in journal (Refereed)
  • 122.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bäckvall, Jan-E.
    Synthesis of Heterocyclic Natural Products via Regio- and Stereocontrolled Palladium-Catalyzed Reactions1996In: Advances in Heterocyclic Natural Product Synthesis, JAI Press Inc, Greenwich , 1996, p. 179-215Chapter in book (Refereed)
  • 123.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Regio- and Stereoselective Deuteration of Allylic Chlorides Controlled by Neighboring Alcohol or Ether Groups1996In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 61, no 12, p. 4154-4156Article in journal (Refereed)
  • 124.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Guijarro, David
    Tanner, David
    Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines1997In: J. Org. Chem., no 62, p. 7364-7375Article in journal (Refereed)
  • 125.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Guijarro, David
    Tanner, David
    Simple Aziridino Alcohols as Chiral Ligands. Enantioselective Additions of Diethylzinc to N-Diphenylphosphinoylimines1996In: Synlett, no 8, p. 727-728Article in journal (Refereed)
  • 126.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Harden, Adrian
    Tanner, David
    Norrby, Per-Ola
    Studies of Allylic Substitution Catalysed by a Palladium Complex of a C2-Symmetric Bis(aziridine): Preparation and NMR Spectroscopic Investigation of a Chiral n-Allyl Species1995In: Chem. Eur. J., no 1, p. 12-16Article in journal (Refereed)
  • 127.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Johansson, Fredrik
    Tanner, David
    Enantioselective Addition of Organolithium Reagents to Imines Mediated by C2-Symmetric Bis(aziridine) Ligands1998In: Tetrahedron, no 54, p. 11549-11566Article in journal (Refereed)
  • 128.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Nilsson, Ylva
    Bäckvall, Jan-E.
    Palladium-Catalyzed Oxaspirocyclizations1994In: Tetrahedron, Vol. 50, no 2, p. 559-572Article in journal (Refereed)
  • 129.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Schab, Szymon
    Mechanism of the Palladium-Catalyzed Elimination of Acetic Acid from Allylic Acetates1995In: Organometallics, Vol. 14, no 1, p. 1-Article in journal (Refereed)
  • 130.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Schink, Hans
    Österlund, Krister
    Asymmetric Total Synthesis of (+)-Tolterodine, a New Muscarinic Receptor Antagonist, via Copper-Assisted Asymmetric Conjugate Addition of Aryl Grignard Reagents to 3-Phenyl-prop-2-enoyl-oxazolidinones1998In: J. Org. Chem., no 63, p. 8067-8070Article in journal (Refereed)
  • 131.
    Andersson, Pher
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Sharpless, K. Barry
    A Dramatic Ligand Effect on the Relative Reactive Reactivites of Substituted Alkenes with Osmium Tetroxide1993In: J. Am. Chem. Soc., no 115, p. 7047-7048Article in journal (Refereed)
  • 132.
    Andersson, Samir
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sun, Licheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    An efficient water oxidation system based on supramolecular assembly of molecular catalyst and cucurbit[7]urilManuscript (preprint) (Other academic)
  • 133.
    Andersson, Samir
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zou, Dapeng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zhang, Rong
    Sun, Shiguo
    Sun, Licheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Light driven formation of a supramolecular system with three CB 8 s locked between redox-active Ru(bpy)(3) complexes2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 17, p. 3605-3609Article in journal (Refereed)
    Abstract [en]

    Three CB[8]s have been reversibly locked between two Ru(bpy)(3)-viologen complexes by light driven electron transfer reactions.

  • 134. Andersson, Samir
    et al.
    Zou, Dapeng
    Zhang, Rong
    Sun, Shiguo
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Selective positioning of CB[8] on two linked viologens and electrochemically driven movement of the host molecule2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 8, p. 1163-1172Article in journal (Refereed)
  • 135. Andersson, Theresa
    et al.
    Lundquist, Martin
    Dolphin, Gunnar T.
    Enander, Karin
    Jonsson, Bengt-Harald
    Nilsson, Jonas W.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Cooperative binding of human Carbonic Anhydrase II by functionalized folded polypeptide receptors2005In: Chem. Biol., no 12, p. 1245-1252Article in journal (Refereed)
  • 136. Andre, Sabine
    et al.
    Pei, Zichao
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Siebert, Hans-Christian
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Gabius, Hans-Joachim
    Glycosyldisulfides from Dynamic Combinatorial Libraries as O-Glycoside Mimetics for Plant and Endogenous Lectins: Their Reactivities in Solid-Phase and Cell Assays and Conformational Analysis by Molecular Dynamics Simulations2006In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, Vol. 14, p. 6314-6326Article in journal (Refereed)
    Abstract [en]

    Dynamic combinatorial library design exploiting the thiol-disulfide exchange readily affords access to glycosyldisulfides. In order to reveal lectin-binding properties of this type of non-hydrolyzable sugar derivative, libraries originating from a mixture of common building blocks of natural glycans and thiocompounds were tested against three plant agglutinins with specificity to galactose, fucose or N-acetylgalactosamine, respectively, in a solid-phase assay. Extent of lectin binding to matrix-immobilized neoglycoprotein presenting the cognate sugar could be reduced, and evidence for dependence on type of carbohydrate was provided by dynamic deconvolution. Glycosyldisulfides also maintained activity in assays of increased physiological relevance, that is, using native tumor cells and also adding to the test panel an endogenous lectin (galectin-3) involved in tumor spread and cardiac dysfunction. N-Acetylgalactosamine was pinpointed as the most important building block of libraries for the human lectin and the digalactoside as most potent compound acting on the toxic mistletoe agglutinin which is closely related to the biohazard ricin. Because this glycosyldisulfide, which even surpasses lactose in inhibitory capacity, rivals thiodigalactoside as inhibitor, their degrees of intramolecular flexibility were comparatively analyzed by computational calculations. Molecular dynamics runs with explicit consideration of water molecules revealed a conspicuously high degree of potential for shape alterations by the disulfide's three-bond system at the interglycosidic linkage. The presented evidence defines glycosyldisulfides as biologically active ligands for lectins

  • 137.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is divided into six parts, all centered around the development of dynamic (i.e., reversibly interacting) systems of molecules and their applications in dynamic combinatorial chemistry (DCC) and organic synthesis.

    Part one offers a general introduction, as well as a more detailed description of DCC, being the central concept of this thesis. Part two explores the potential of the nitroaldol reaction as a tool for constructing dynamic systems, employing benzaldehyde derivatives and nitroalkanes. This reaction is then applied in part three where a dynamic nitroaldol system is resolved by lipase-catalyzed transacylation, selecting two out of 16 components.

    In part four, reaction and crystallization driven DCC protocols are developed and demonstrated. The discovery of unexpected crystalline properties of certain pyridine β-nitroalcohols is used to resolve a dynamic system and further expanded into asynthetic procedure. Furthermore, a previously unexplored tandem nitroaldol-iminolactone rearrangement reaction between 2-cyanobenzaldehyde and primarynitroalkanes is used for the resolution of dynamic systems. It is also coupled with diastereoselective crystallization to demonstrate the possibility to combine several selection processes. The mechanism of this reaction is investigated and a synthetic protocol is developed for asymmetric synthesis of 3-substituted isoindolinones.

    Part five continues the exploration of tandem reactions by combining dynamic hemithioacetal or cyanohydrin formation with intramolecular cyclization to synthesize a wide range of 3-functionalized phthalides.

    Finally, part six deals with the construction of a laboratory experiment to facilitate the introduction of DCC in undergraduate chemistry education. The experiment is based on previous work in our group and features an acetylcholinesterase-catalyzed resolution of a dynamic transthioacylation system.

  • 138.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process2008In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, no 9, p. 3593-3595Article in journal (Refereed)
    Abstract [en]

    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial library is presented. In a one-pot experiment, an initial nitroaldol equilibrium was kinetically driven by a tandem reaction resulting in a subsequent dynamic library of diastereoisomers. This library was then further driven by a phase change, resulting in amplification and isolation of a highly diastereomerically enriched and synthetically interesting isoindolinone.

  • 139.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Introducing Dynamic Combinatorial Chemistry: Probing the Substrate Selectivity of Acetylcholinesterase2010In: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, no 11, p. 1248-1251Article in journal (Refereed)
  • 140.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Rahm, Martin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation2010In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 17, p. 5882-5887Article in journal (Refereed)
    Abstract [en]

    The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.

  • 141.
    Angles d'Ortoli, Thibault
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Assembling and Unraveling Carbohydrates Structures: Conformational analysis of synthesized branched oligosaccharides2016Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Advances in the elaboration of vaccines and enzyme inhibitors rely on acquiring more knowledge about protein-carbohydrate binding events. Furthermore, the relationships between biological function and the three-dimensional properties of large glycans can be studied by focusing on the structural components they contained, namely, by scaling down the system under analysis. Chemical methods are useful assets as they allow the isolation and determination of epitopes; these small and recognizable fragments that lead to very specific interactions. In this thesis, biologically relevant saccharides were obtained using recently developed concepts in carbohydrate synthesis and NMR spectroscopy was used to unravel their conformational preferences.

    In paper I, the convergent synthesis of the tetrasaccharide found in the natural product solaradixine is described. Reactivity enhanced disaccharide glycosyl donors were coupled to a disaccharide acceptor in a 2 + 2 fashion. The computer program CASPER was subsequently used to verify the synthesized structure.

    The conformation arming concept employed in paper I was further investigated in paper II. An NMR-based methodology enabled the determination of the ring conformations of a set of donors. Subsequently, glycosylation reactions were performed and yields were correlated to donors ring shapes. Perturbations in the rings shape caused by bulky silyl ether protective groups were sufficient to boost the potency of several donors. As a matter of fact, complex branched oligosaccharides could be obtained in good to excellent yields.

    In paper III, NMR spectroscopy observables were measured to elucidate the ring shape, the mutual orientation of the rings across the glycosidic bond and the positions of the side chains of 5 trisaccharides found in larger structures. With the aid of molecular dynamics simulations, their overall conformational propensities were revealed.

    Finally, the software CASPER prediction skills were improved by adding, inter alia, NMR information of synthesized mono- and disaccharides to its database. Unassigned chemical shifts from polysaccharides served as input to challenge its ability to solve large carbohydrate structures.

  • 142.
    Angles d'Ortoli, Thibault
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hamark, Christoffer
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Structure-Reactivity Relationships of Conformationally Armed Disaccharide Donors and Their Use in the Synthesis of a Hexasaccharide Related to the Capsular Polysaccharide from Streptococcus pneumoniae Type 372017In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 15, p. 8123-8140Article in journal (Refereed)
    Abstract [en]

    To advance the field of glycobiology, efficient synthesis methods of oligosaccharides and glycoconjugates are a requisite. In glycosylation reactions using superarmed donors, both selectivity and reactivity issues must be considered, and we herein investigate these aspects for differently protected beta-linked 2-O-glycosylated glucosyl donors carrying bulky tert-butyldimethylsilyl groups to different extents. The acceptors in reactions being secondary alcohols presents a challenging situation with respect to steric crowding. Conformational pyranose ring equilibria of the superarmed disaccharide donors with axial-rich substituents contained skew and boat conformations, and three-state models were generally assumed. With NIS/TfOH as the promotor, 2,6-di-tert-butyl-4-methylpyridine as the base, and a dichloromethane/toluene solvent mixture, ethyl 1-thio-beta-d-glucosyl disaccharide donors having 6-O-benzyl group(s) besides tert-butyldimethylsilyl groups were efficiently coupled at -40 degrees C to the hydroxyl group at position 3 of glucopyranosyl acceptors to form beta-(1 -> 2),beta-(1 -> 3)-linked trisaccharides, isolated in excellent 95% yield. The more axial-rich donors in skew and boat conformations are thus preorganized closer to the assumed transition state in these glycosylation reactions. The developed methodology was subsequently applied in the synthesis of a multibranched hexasaccharide related to the capsular polysaccharide from Streptococcus pneumoniae type 37, which consists of a beta-(1 -> 3)-linked backbone and a beta-(1 -> 2)-linked side chain of D-glucosyl residues in disaccharide repeating units.

  • 143.
    Angles d'Ortoli, Thibault
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mobarak, Hani
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ståhle, Jonas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hamark, Christoffer
    Fontana, Carolina
    Engström, Olof
    Apostolica, Patricia
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Complete 1H and 13C NMR chemical shift assignments of mono- to tetrasaccharides as basis for NMR chemical shift predictions of oligo- and polysaccharides using the computer program CASPERManuscript (preprint) (Other academic)
  • 144.
    Angles d'Ortoli, Thibault
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sjöberg, Nils A.
    Vasiljeva, Polina
    Lindman, Jonas
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bergenstråhle-Wohlert, Malin
    Wohlert, Jakob
    Temperature Dependence of Hydroxymethyl Group Rotamer Populations in Cellooligomers2015In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 119, no 30, p. 9559-9570Article in journal (Refereed)
    Abstract [en]

    Empirical force fields for computer simulations of carbohydrates are often implicitly assumed to be valid also at temperatures different from room temperature for which they were optimited: Herein, the temperature dependence of the hydroxymethyl group rotamer populations in short oligogaccharides is invegtigated using Molecular dynamics simulations and NMR spectroscopy. Two oligosaccharides, methyl beta-cellobioside and beta-cellotetraose were simulated using three different carbohydrate force fields (CHARMM C35, GLYCAM06, and GROMOS 56A(carbo)) in combination with different water models (SPC, SPC/E, and TIP3P) using replica exchange molecular dynamics simulations. For comparison, hydroxymethyl group rotamer populations were investigated for methyl beta-cellobioside and cellopentaose based- on measured NMR (3)J(H5,H6) coupling constants, in the latter case by using a chemical shift selective NMR-filter. Molecular dynamics simulations in combination with NMR spectroscopy show that the temperature dependence of the hydroxymethyl rotamer population in these short cellooligomers, in the range 263-344 K, generally becomes exaggerated in simulations when compared to experimental data, but also that it is dependent on simulation conditions, and most notably properties of the water model.

  • 145.
    Angles d'Ortoli, Thibault
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of the tetrasaccharide glycoside moiety of Solaradixine and rapid NMR-based structure verification using the program CASPER2016In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 72, no 7, p. 912-927Article in journal (Refereed)
    Abstract [en]

    The major glycoalkaloid in the roots of Solanum laciniatum is Solaradixine having the branched tetrasaccharide beta-D-Glcp-(1 -> 2)-beta-D-Glcp-(1 -> 3)[alpha-L-Rhap-(1 -> 2)]-beta-D-Galp linked to O3 of the steroidal alkaloid Solasodine. We herein describe the synthesis of the methyl glycoside of the tetrasaccharide using a super-armed disaccharide as a donor molecule. A 2-(naphthyl)methyl protecting group was used in the synthesis of the donor since it was tolerant to a wide range of reaction conditions. The 6-O-benzylated-hexa-O-tert-butyldimethylsilyi-protected beta-D-Glcp-(1 -> 2)-beta-D-Glcp-SEt donor, which avoided 1,6-anydro formation, was successfully glycosylated at O3 of a galactoside acceptor molecule. However, subsequent glycosylation at O2 by a rhamnosyl donor was unsuccessful and instead a suitably protected alpha-L-Rhap(1 -> 2)-beta-D-Galp-OMe disaccharide was used as the acceptor molecule together with a super-armed beta-D-Glcp-(1 -> 2)-beta-D-Glcp-SEt donor in the glycosylation reaction, to give a tetrasaccharide in a yield of 55%, which after deprotection resulted in the target molecule, the structure of which was verified by the NMR chemical shift prediction program CASPER.

  • 146.
    Ankarloo, Jonas
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wikman, Susanne
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Escherichia coli mar and acrAB Mutants Display No Tolerance to Simple Alcohols2010In: International Journal of Molecular Sciences, ISSN 1422-0067, E-ISSN 1422-0067, Vol. 11, no 4, p. 1403-1412Article in journal (Refereed)
    Abstract [en]

    The inducible Mar phenotype of Escherichia coli is associated with increased tolerance to multiple hydrophobic antibiotics as well as some highly hydrophobic organic solvents such as cyclohexane, mediated mainly through the AcrAB/TolC efflux system. The influence of water miscible alcohols ethanol and 1-propanol on a Mar constitutive mutant and a mar deletion mutant of E. coli K-12, as well as the corresponding strains carrying the additional acrAB deletion, was investigated. In contrast to hydrophobic solvents, all strains were killed in exponential phase by 1-propanol and ethanol at rates comparable to the parent strain. Thus, the Mar phenotype does not protect E. coli from killing by these more polar solvents. Surprisingly, AcrAB does not contribute to an increased alcohol tolerance. In addition, sodium salicylate, at concentrations known to induce the mar operon, was unable to increase 1-propanol or ethanol tolerance. Rather, the toxicity of both solvents was increased in the presence of sodium salicylate. Collectively, the results imply that the resilience of E. coli to water miscible alcohols, in contrast to more hydrophobic solvents, does not depend upon the AcrAB/TolC efflux system, and suggests a lower limit for substrate molecular size and functionality. Implications for the application of microbiological systems in environments containing high contents of water miscible organic solvents, e. g., phage display screening, are discussed.

  • 147.
    Ankerfors, M.
    et al.
    RISE, Innventia.
    Duker, E.
    Lindström, T.
    RISE, Innventia.
    Topo-chemical modification of fibres by grafting of carboxymethyl cellulose in pilot scale2013In: Nordic Pulp and Paper Research Journal, ISSN 0283-2631 , no 1, p. 6-14Article in journal (Refereed)
  • 148.
    Antoni G., Amschler H., Zech K., Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis of [18F]labelled roflumilast using difluoro[18F]bromo methane as alkylating agent2001In: Synthesis and Applications of Isotopically LabelledArticle in journal (Refereed)
  • 149.
    Antoni G., Ögren M., Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Enzymes as catalysts in labelling synthesis using short-lived radionuclides2001In: Synthesis and Applications of Isotopically LabelledArticle in journal (Refereed)
  • 150.
    Antoni, Gunnar
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Kihlberg, T.
    Långström, B.
    11C: Labelling chemistry and labelled compounds2003In: Handbook Chem03_0302, 2003, no 332, p. 119-165Chapter in book (Refereed)
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