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  • 101.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Koch-Schmidt, Ann-Christin
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Ohlson, Sten
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Study of the Nature of Recognition in Molecularly Imprinted Polymers1996Inngår i: J. Mol. Recogn., Vol. 9, p 675-682Artikkel i tidsskrift (Fagfellevurdert)
  • 102.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Nicholls, Ian A.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Molecular Imprinting. Recent innovations in synthetic polymer receptor and enzyme mimics1997Inngår i: Recent Research Developments in Pure and Applied Chemistry, Vol. 1, s. 133-157Artikkel i tidsskrift (Fagfellevurdert)
  • 103.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Nicholls, Ian A.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Spectroscopic evaluation of molecular imprinting polymerization systems1997Inngår i: Bioorganic Chemistry, Vol. 25, s. 203-211Artikkel i tidsskrift (Fagfellevurdert)
  • 104.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Nicholls, Ian A.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    The development of molecular imprinting2000Annet (Annet vitenskapelig)
  • 105.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Piletsky, S A
    Mosbach, K
    Koch-Schmidt, Ann-Christin
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Nicholls, Ian A.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Novel recognition elements for improved molecularly imprinted polymer stereoselectivity1997Konferansepaper (Fagfellevurdert)
  • 106.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Ramström, O
    Crown Ethers as a Tool for the Preparation of Molecularly Imprinted Polymers1998Inngår i: Journal of Molecular Recognition, Vol. 11, s. 103-106Artikkel i tidsskrift (Fagfellevurdert)
  • 107.
    Andersson, Håkan S.
    et al.
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Ramström, Olof
    Lund University.
    Crown ethers as a tool for the preparation of molecularly imprinted polymers1997Konferansepaper (Annet vitenskapelig)
  • 108.
    Andersson, Ida E.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Modified Glycopeptides Targeting Rheumatoid Arthritis: Exploring molecular interactions in class II MHC/glycopeptide/T-cell receptor complexes2011Doktoravhandling, med artikler (Annet vitenskapelig)
    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.

  • 109. Andersson, L I
    et al.
    Nicholls, Ian Alan
    Högskolan i Kalmar, Naturvetenskapliga institutionen.
    Mosbach, K
    Immunoassays using molecularly imprinted polymers1995Inngår i: Immunoanalysis of agrochemicals: emerging technologies / [ed] Judd O. Nelson, Alexander E. Karu and Rosie B. Wong, American Chemical Society (ACS), 1995, s. 89-97Konferansepaper (Annet vitenskapelig)
  • 110.
    Andersson, Linnéa
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi. Oorganisk kemi.
    Exploring expandable microspheres as a novel pore former in gel-cast macroporous alumina2008Licentiatavhandling, monografi (Annet vitenskapelig)
    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.

  • 111.
    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 Change2007Inngår i: Tenside Surfactants Detergents, ISSN 0932-3414, E-ISSN 2195-8564, Vol. 44, nr 6, s. 366-372Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 112.
    Andersson, Mats
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Determination of the structures of three bacterial polysaccharides and synthesis and use of new spacers for glycoconjugate formation1993Doktoravhandling, med artikler (Annet vitenskapelig)
    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.

  • 113.
    Andersson, Nina
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Mesostructured materials: Synthesis towards applications2007Doktoravhandling, med artikler (Annet vitenskapelig)
    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.

  • 114.
    Andersson, P.G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Development of New Methodology for th Preparation of Optically Active Alcohols2004Inngår i: Pure Appl. Chem., nr 76, s. 547-Artikkel i tidsskrift (Fagfellevurdert)
  • 115.
    Andersson, Pher
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Development of a new methodology for the preparation of optically active alcohols*2004Inngår i: Pure Appl. Chem., Vol. 76, nr 3, s. 547-555Artikkel i tidsskrift (Fagfellevurdert)
  • 116.
    Andersson, Pher
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    On the Stereochemical Outcome of the McMurry Coupling of Acetophenone. A Reinvestigation1994Inngår i: Tetrahedron Letters, Vol. 35, nr 16, s. 2609-2610Artikkel i tidsskrift (Fagfellevurdert)
  • 117.
    Andersson, Pher
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Regio- and Stereoselective Deuteration of Allylic Chlorides Controlled by Neighboring Alcohol or Ether Groups1996Inngår i: J. Org. Chem., nr 61, s. 4154-4156Artikkel i tidsskrift (Fagfellevurdert)
  • 118.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Aranyos, Attila
    Palladium-Mediated Stereo- and Regioselective Tandem-Cyclization-Carbonylations of 1,3-dienes1994Inngår i: Tetrahedron Letters, Vol. 35, nr 25, s. 4441-4444Artikkel i tidsskrift (Fagfellevurdert)
  • 119.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Bäckvall, Jan-E.
    Palladium-Catalyzed Tandem Cyclization of 4,6- and 5,7-Diene Amides. A New Route towards the Pyrrolizidine and Indolizidine Alkaloids1992Inngår i: J. Am. Chem. Soc., Vol. 114, nr 22, s. 8696-8698Artikkel i tidsskrift (Fagfellevurdert)
  • 120.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Bäckvall, Jan-E.
    Synthesis of Furanoid Terpenes via an Efficient Palladium-Catalyzed Cyclization of 4,6-Dienols1991Inngår i: J. Org. Chem., Vol. 56, nr 18, s. 5349-5353Artikkel i tidsskrift (Fagfellevurdert)
  • 121.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Bäckvall, Jan-E.
    Synthesis of Heterocyclic Natural Products via Regio- and Stereocontrolled Palladium-Catalyzed Reactions1996Inngår i: Advances in Heterocyclic Natural Product Synthesis, JAI Press Inc, Greenwich , 1996, s. 179-215Kapittel i bok, del av antologi (Fagfellevurdert)
  • 122.
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Regio- and Stereoselective Deuteration of Allylic Chlorides Controlled by Neighboring Alcohol or Ether Groups1996Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 61, nr 12, s. 4154-4156Artikkel i tidsskrift (Fagfellevurdert)
  • 123.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Guijarro, David
    Tanner, David
    Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines1997Inngår i: J. Org. Chem., nr 62, s. 7364-7375Artikkel i tidsskrift (Fagfellevurdert)
  • 124.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Guijarro, David
    Tanner, David
    Simple Aziridino Alcohols as Chiral Ligands. Enantioselective Additions of Diethylzinc to N-Diphenylphosphinoylimines1996Inngår i: Synlett, nr 8, s. 727-728Artikkel i tidsskrift (Fagfellevurdert)
  • 125.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi 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 Species1995Inngår i: Chem. Eur. J., nr 1, s. 12-16Artikkel i tidsskrift (Fagfellevurdert)
  • 126.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Johansson, Fredrik
    Tanner, David
    Enantioselective Addition of Organolithium Reagents to Imines Mediated by C2-Symmetric Bis(aziridine) Ligands1998Inngår i: Tetrahedron, nr 54, s. 11549-11566Artikkel i tidsskrift (Fagfellevurdert)
  • 127.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Nilsson, Ylva
    Bäckvall, Jan-E.
    Palladium-Catalyzed Oxaspirocyclizations1994Inngår i: Tetrahedron, Vol. 50, nr 2, s. 559-572Artikkel i tidsskrift (Fagfellevurdert)
  • 128.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Schab, Szymon
    Mechanism of the Palladium-Catalyzed Elimination of Acetic Acid from Allylic Acetates1995Inngår i: Organometallics, Vol. 14, nr 1, s. 1-Artikkel i tidsskrift (Fagfellevurdert)
  • 129.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi 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-oxazolidinones1998Inngår i: J. Org. Chem., nr 63, s. 8067-8070Artikkel i tidsskrift (Fagfellevurdert)
  • 130.
    Andersson, Pher
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen. Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Sharpless, K. Barry
    A Dramatic Ligand Effect on the Relative Reactive Reactivites of Substituted Alkenes with Osmium Tetroxide1993Inngår i: J. Am. Chem. Soc., nr 115, s. 7047-7048Artikkel i tidsskrift (Fagfellevurdert)
  • 131.
    Andersson, Samir
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Sun, Licheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    An efficient water oxidation system based on supramolecular assembly of molecular catalyst and cucurbit[7]urilManuskript (preprint) (Annet vitenskapelig)
  • 132.
    Andersson, Samir
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zou, Dapeng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Zhang, Rong
    Sun, Shiguo
    Sun, Licheng
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Light driven formation of a supramolecular system with three CB 8 s locked between redox-active Ru(bpy)(3) complexes2009Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, nr 17, s. 3605-3609Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

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

  • 133. Andersson, Samir
    et al.
    Zou, Dapeng
    Zhang, Rong
    Sun, Shiguo
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sun, Licheng
    Selective positioning of CB[8] on two linked viologens and electrochemically driven movement of the host molecule2009Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 8, s. 1163-1172Artikkel i tidsskrift (Fagfellevurdert)
  • 134. Andersson, Theresa
    et al.
    Lundquist, Martin
    Dolphin, Gunnar T.
    Enander, Karin
    Jonsson, Bengt-Harald
    Nilsson, Jonas W.
    Baltzer, Lars
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi II.
    Cooperative binding of human Carbonic Anhydrase II by functionalized folded polypeptide receptors2005Inngår i: Chem. Biol., nr 12, s. 1245-1252Artikkel i tidsskrift (Fagfellevurdert)
  • 135. Andre, Sabine
    et al.
    Pei, Zichao
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Siebert, Hans-Christian
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    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 Simulations2006Inngår i: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, Vol. 14, s. 6314-6326Artikkel i tidsskrift (Fagfellevurdert)
    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

  • 136.
    Angelin, Marcus
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications2010Doktoravhandling, med artikler (Annet vitenskapelig)
    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.

  • 137.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process2008Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, nr 9, s. 3593-3595Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 138.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Larsson, Rikard
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Vongvilai, Pornrapee
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
    Introducing Dynamic Combinatorial Chemistry: Probing the Substrate Selectivity of Acetylcholinesterase2010Inngår i: Journal of Chemical Education, ISSN 0021-9584, E-ISSN 1938-1328, Vol. 87, nr 11, s. 1248-1251Artikkel i tidsskrift (Fagfellevurdert)
  • 139.
    Angelin, Marcus
    et al.
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Rahm, Martin
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Fischer, Andreas
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Brinck, Tore
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Ramström, Olof
    KTH, Skolan för kemivetenskap (CHE), Kemi.
    Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation2010Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, nr 17, s. 5882-5887Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 140.
    Angles d'Ortoli, Thibault
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Assembling and Unraveling Carbohydrates Structures: Conformational analysis of synthesized branched oligosaccharides2016Doktoravhandling, med artikler (Annet vitenskapelig)
    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.

  • 141.
    Angles d'Ortoli, Thibault
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hamark, Christoffer
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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 372017Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, nr 15, s. 8123-8140Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 142.
    Angles d'Ortoli, Thibault
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mobarak, Hani
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ståhle, Jonas
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hamark, Christoffer
    Fontana, Carolina
    Engström, Olof
    Apostolica, Patricia
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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 CASPERManuskript (preprint) (Annet vitenskapelig)
  • 143.
    Angles d'Ortoli, Thibault
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sjöberg, Nils A.
    Vasiljeva, Polina
    Lindman, Jonas
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bergenstråhle-Wohlert, Malin
    Wohlert, Jakob
    Temperature Dependence of Hydroxymethyl Group Rotamer Populations in Cellooligomers2015Inngår i: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 119, nr 30, s. 9559-9570Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 144.
    Angles d'Ortoli, Thibault
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis of the tetrasaccharide glycoside moiety of Solaradixine and rapid NMR-based structure verification using the program CASPER2016Inngår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 72, nr 7, s. 912-927Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 145.
    Ankarloo, Jonas
    et al.
    Linnéuniversitetet, Fakultetsnämnden för naturvetenskap och teknik, Institutionen för naturvetenskap, NV.
    Wikman, Susanne
    Linnéuniversitetet, Fakultetsnämnden för naturvetenskap och teknik, Institutionen för naturvetenskap, NV.
    Nicholls, Ian A.
    Linnéuniversitetet, Fakultetsnämnden för naturvetenskap och teknik, Institutionen för naturvetenskap, NV.
    Escherichia coli mar and acrAB Mutants Display No Tolerance to Simple Alcohols2010Inngår i: International Journal of Molecular Sciences, ISSN 1422-0067, E-ISSN 1422-0067, Vol. 11, nr 4, s. 1403-1412Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 146.
    Ankerfors, M.
    et al.
    RISE, Innventia.
    Duker, E.
    Lindström, T.
    RISE, Innventia.
    Topo-chemical modification of fibres by grafting of carboxymethyl cellulose in pilot scale2013Inngår i: Nordic Pulp and Paper Research Journal, ISSN 0283-2631 , nr 1, s. 6-14Artikkel i tidsskrift (Fagfellevurdert)
  • 147.
    Antoni G., Amschler H., Zech K., Långström B.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Synthesis of [18F]labelled roflumilast using difluoro[18F]bromo methane as alkylating agent2001Inngår i: Synthesis and Applications of Isotopically LabelledArtikkel i tidsskrift (Fagfellevurdert)
  • 148.
    Antoni G., Ögren M., Långström B.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Enzymes as catalysts in labelling synthesis using short-lived radionuclides2001Inngår i: Synthesis and Applications of Isotopically LabelledArtikkel i tidsskrift (Fagfellevurdert)
  • 149.
    Antoni, Gunnar
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Kihlberg, T.
    Långström, B.
    11C: Labelling chemistry and labelled compounds2003Inngår i: Handbook Chem03_0302, 2003, nr 332, s. 119-165Kapittel i bok, del av antologi (Fagfellevurdert)
  • 150.
    Antoni, Gunnar
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen.
    Långström, Bengt
    Asymmetric synthesis of L-2-amino[3-11C]butyric acid, L-[3-11C]norvaline and L-[3-11C]valine.1987Inngår i: Acta Chemica Scandinavica, ISSN 0904-213X, E-ISSN 1902-3103, Vol. B41, s. 511-Artikkel i tidsskrift (Fagfellevurdert)
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