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  • 1.
    Acharya, Parag
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Studies on the Non-covalent Interactions (Stereoelectronics, Stacking and Hydrogen Bonding) in the Self-assembly of DNA and RNA2003Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is based on ten publications (Papers I-X). The phosphodiester backbone makes DNA or RNA to behave as polyelectrolyte, the pentose sugar gives the flexibility, and the aglycones promote the self-assembly or the ligand-binding process. The hydrogen bonding, stacking, stereoelectronics and hydration are few of the important non-covalent forces dictating the self-assembly of DNA/RNA. The pH-dependent thermodynamics clearly show (Papers I and II) that a change of the electronic character of aglycone modulates the conformation of the sugar moiety by the tunable interplay of stereoelectronic anomeric and gauche effects, which are further transmitted to steer the sugar-phosphate backbone conformation in a cooperative manner. 3'-anthraniloyl adenosine (a mimic of 3'-teminal CCAOH of the aminoacyl-tRNAPhe) binds to EF-Tu*GTP in preference over 2'-anthraniloyl adenosine, thereby showing (Paper III) that the 2’-endo sugar conformation is a more suitable mimic of the transition state geometry than the 3’-endo conformation in discriminating between correctly and incorrectly charged aminoacyl-tRNAPhe by EF-Tu during protein synthesis. The presence of 2'-OH in RNA distinguishes it from DNA both functionally as well as structurally. This work (Paper IV) provides straightforward NMR evidence to show that the 2'-OH is intramolecularly hydrogen bonded with the vicinal 3'-oxygen, and the exposure of the 3'-phosphate of the ribonucleotides to the bulk water determines the availability of the bound water around the vicinal 2'-OH, which then can play various functional role through inter- or intramolecular interactions. The pH-dependent 1H NMR study with nicotinamide derivatives demonstrates (Paper V) that the cascade of intramolecular cation (pyridinium)-π(phenyl)-CH(methyl) interaction in edge-to-face geometry is responsible for perturbing the pKa of the pyridine-nitrogen as well as for the modulation of the aromatic character of the neighboring phenyl moiety, which is also supported by the T1 relaxation studies and ab initio calculations. It has been found (Papers VI-IX) that the variable intramolecular electrostatic interaction between electronically coupled nearest neighbor nucleobases (steered by their respective microenvironments) can modulate their respective pseudoaromatic characters. The net result of this pseudoaromatic cross-modulation is the creation of a unique set of aglycones in an oligo or polynucleotide, whose physico-chemical properties are completely dependent upon the propensity and geometry of the nearest neighbor interactions (extended genetic code). The propagation of the interplay of these electrostatic interactions across the hexameric ssDNA chain is considerably less favoured (effectively up to the fourth nucleobase) compared to that of the isosequential ssRNA (up to the sixth nucleobase). The dissection of the relative strength of basepairing and stacking in a duplex shows that stability of DNA-DNA duplex weakens over the corresponding RNA-RNA duplexes with the increasing content of A-T/U base pairs, while the strength of stacking of A-T rich DNA-DNA duplex increases in comparison with A-U rich sequence in RNA-RNA duplexes (Paper X).

  • 2.
    Alpe, Marianne
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of oligosaccharides related to the capsular polysaccharides of Streptococcus pneumoniae serotype 9 and of Cryptococcus neoformans2003Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In the present investigation, synthesis of oligosaccharides corresponding to structural elements present in the capsular polysaccharides of Streptococcus pneumoniae and Cryptococcus neoformans has been achieved. The first two sections describe the synthesis of spacer-equipped oligosaccharides corresponding to structures from the CPS of Streptococcus pneumoniae serotypes 9N, 9A and 9L, the production of which involved synthetic challenges such as the construction of β-ManNAc and α-GlcA linkages. The former challenge was met by employing azide displacement of a 2-O-triflate substituent on a β-glucoside, whereas the latter task was accomplished utilizing thioethyl glucuronic acid donors in the presence of various promoters. The pentasaccharide product obtained correspond to the complete repeating unit of the CPS of serotype 9A.

    The last two sections of this thesis describe the construction of thioglycoside di- and trisaccharide building blocks containing α-Man, β-Xyl, β-GlcA and 6-O-acetyl motifs, as well as subsequent assembly of these building blocks into oligosaccharides corresponding to the repeating units of the capsular polysaccharide of the yeast Cryptococcus neoformans. The GlcA moiety was introduced via trichloroacetimidate coupling involving the peracetylated glucuronic acid methyl ester donor, after which the subsequent necessary benzylation was performed with the di- and trisaccharides. All of the target oligosaccharides were synthesized as amino-spacer glycosides in order to make conjugation to a carrier protein possible.

  • 3.
    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)
  • 4.
    Arvidsson, Per
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Frackenpohl, J
    Seebach, D
    Syntheses an CD-Spectroscopic Investigations of Longer-Chain B-Peptides: Preparation by Solid-Phase Couplings of Single Amino Acids, Dipeptides, and Tripeptides2003In: Helvetica Chemica Acta, no 86, p. 1552-1553Article in journal (Refereed)
  • 5.
    Arvidsson, Per
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Ryder, N
    Weiss, M
    Gross, G
    Kretz, O
    Woessner, R
    Seebach, D
    Antibiotic and Hemolytic Activity of a B2/B3 Peptide Capable of Folding into a 12/10-Helical Secondary Structure2003In: ChemBioChem, no 4, p. 1345-1347Article in journal (Refereed)
  • 6.
    Berglund, Per
    et al.
    KTH, Superseded Departments, Biotechnology.
    Branneby, Cecilia
    Svedendahl Humble, Maria
    KTH, School of Biotechnology (BIO), Biochemistry (closed 20130101).
    Carlqvist, Peter
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry (closed 20110630).
    Magnusson, Anders
    Hult, Karl
    KTH, School of Biotechnology (BIO), Biochemistry (closed 20130101).
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry (closed 20110630).
    Aldol and Michael additions catalyzed by a rationally redesigned hydrolytic enzyme2003In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 226, no 2, p. U155-U156Article in journal (Refereed)
  • 7.
    Bergman, Jan
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Engqvist, Robert
    Karolinska Institute.
    Stålhandske, C
    Chemical Centre, Lund.
    Wallberg, H
    KTH.
    Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine2003In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 7, p. 1033-1048Article in journal (Refereed)
  • 8.
    Bergström, M.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Awad, R.
    Estrada, S., Malman, J.
    Lu, L., Lendvai, G.
    Bergström-Pettermann, E., Långström, B.
    Autoradiography with positron emitting isotopes in positron emission tomography tracer discovery2003In: Mol Imaging Biol., Vol. 6, no 460, p. 390-396Article in journal (Refereed)
  • 9.
    Berlin, S
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Ericsson, C
    Engman, L.
    Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones2003In: J. Org. Chem., no 68, p. 8386-Article in journal (Refereed)
  • 10.
    Berlin, Stefan
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Construction of Five-Membered Heterocyclic Compounds via Radical Cyclization2003Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis describes how radical cyclization chemistry can be applied for the construction of heterocyclic compounds.

    In the first part, a series of electron deficient α-phenylselenenylalkenes were prepared via a PhSeCl-addition/HCl-elimination sequence. Allyl- and propargylamines readily underwent conjugate addition to these species to produce pyrrolidines or dihydropyrrol derivatives, after triethylborane initiated reductive radical cyclization in the presence of tris(trimethylsilyl)silane.

    The second part describes a convergent synthesis of the pineal hormone melatonin. The indole nucleus is secured via a tris(trimethylsilyl)silane mediated 5-exo radical cyclization. The protocol provides convenient and simple access to compounds useful for studies of biological activity and structure activity relationships.

    The third part describes construction of substituted tetrahydrofuran-3-ones and pyrrolidin-3-ones. Regioselective ring-opening of epoxides or aziridines with benzeneselenolate/tellurolate, followed by Michael addition to electron deficient alkynes afforded the corresponding O/N-vinylated compounds. The tetrahydrofuran-3-ones and pyrrolidin-3-ones were secured via radical carbonylation/reductive cyclization using pressurized carbon monoxide (80 atm).

    The fourth part is concerned with the effect of an N-protecting group on the cyclization of 2-substituted-3-aza-5-hexenyl radicals. Relative energies for reactants and transition states were determined using density functional calculations. Reactant and transition state conformers leading to cis-product were lower in energy than those leading to trans-product. The results can be explained by the unfavorable 1,2-strain present in chair-equatorial and boat-equatorial conformers.

  • 11.
    Beshara, Soheir
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences, Clinical Chemistry.
    Sörensen, Jens
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Radiology, Oncology and Radiation Science, Section of Nuclear Medicine and PET. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences, Clinical Physiology.
    Lubberink, Mark
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Radiology, Oncology and Radiation Science, Section of Nuclear Medicine and PET.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Radiology, Oncology and Radiation Science, Biomedical Radiation Sciences.
    Långström, Bengt
    PET Centre, University Hospital, Uppsala, Sweden.
    Antoni, Gunnar
    PET Centre, University Hospital, Uppsala, Sweden.
    Danielsson, Bo G.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences, Internal Medicine.
    Lundqvist, Hans
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Radiology, Oncology and Radiation Science, Biomedical Radiation Sciences.
    Pharmacokinetics and red cell utilization of 52Fe/59Fe-labelled iron polymaltose in anaemic patients using positron emission tomography2003In: British Journal of Haematology, ISSN 0007-1048, E-ISSN 1365-2141, Vol. 120, no 5, p. 853-859Article in journal (Other academic)
    Abstract [en]

    Parenteral iron-polysaccharide complexes are increasingly applied. The pharmacokinetics of iron sucrose have been assessed by our group using positron emission tomography (PET). A single intravenous injection of 100 mg iron as iron (III) hydroxide-polymaltose complex, labelled with a tracer in the form of 52Fe/59Fe, was similarly assessed in six patients using PET for about 8 h. Red cell utilization was followed for 4 weeks. Iron polymaltose was similarly distributed to the liver, spleen and bone marrow. However, a larger proportion of this complex was rapidly distributed to the bone marrow. The shorter equilibration phase for the liver, about 25 min, indicates the minimal role of the liver for direct distribution. Splenic uptake also reflected the reticuloendothelial handling of this complex. Red cell utilization ranged from 61% to 99%. Despite the relatively higher uptake by the bone marrow, there was no saturation of marrow transport systems at this dose level. In conclusion, high red cell utilization of iron polymaltose occurred in anaemic patients. The major portion of the injected dose was rapidly distributed to the bone marrow. In addition, the reticuloendothelial uptake of this complex may reflect the safety of polysaccharide complexes. Non-saturation of transport systems to the bone marrow indicated the presence of a large interstitial transport pool, which might possibly be transferrin.

  • 12.
    Blomquist, G.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Engler, H.
    Wall, A.
    Sandell, J.
    Koivisto, P.
    Långström, B.
    Reference tissue methods in analyzing brain uptake of PIB with PET2003In: EANM, Amsterdam, 2003Conference paper (Other scientific)
  • 13.
    Bohl Kullberg E, Carlsson J, Edwards K, Capala J, Sjöberg S, Gedda L.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Introductory Experiments On Ligand Liposomes as Delivery Agents for Boron Neutron Capture Therapy2003In: International Journal of Oncology, no 23, p. 461-467Article in journal (Other scientific)
  • 14.
    Brandt, P
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Andersson, P.G.
    A DFT Exploration of the Enantiolselective Rearrangement of Cyclohexene Oxide to Cyclohexenol2003In: Tetrahedron, no 59, p. 9695-Article in journal (Refereed)
  • 15.
    Brandt P, Hedberg C, Andersson P.G
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    New Mechanistic Insights into the Ir-(phosphano-oxazoline) Catalysed Hydrogenation of Unfunctinalized Olefines: A DFT and Kinetic Study2003In: Chem. Eur. J., no 9, p. 339-Article in journal (Other scientific)
  • 16. Brandt, Peter
    et al.
    Hedberg, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    New Mechanistic Insights into the Iridium-Phosphanooxazoline-Catalyzed Hydrogenation of Unfunctionalized Olefins: A DFT and Kinetic Study2003In: Chem. Eur. J., no 9, p. 339-347Article in journal (Refereed)
    Abstract
  • 17.
    Bratt K, Sunnerheim K, Bryngelsson S, Fagerlund A, Engman L, Andersson R.E, Dimberg L.H
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Avenanthramides in Oats (Avena sativa L.) and Structure-Antioxidant Activity Relationships2003In: J. Agric. Food Chem, no 51, p. 594-Article in journal (Other scientific)
  • 18.
    Bratt, K
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Sunnerheim, K
    Bryngelsson, S
    Fagerlund, A
    Engman, L
    Häll, Dimberg L.
    Avenanthramides in Oats: Structure - Antioxidant Activity Relationsip2003In: J. Agric Food Chem., no 51, p. 594-600Article in journal (Other scientific)
  • 19. Bratt, Katarina
    et al.
    Sunnerheim, Kerstin
    Bryngelsson, Susanne
    Fagerlund, Amelie
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Engman, Lars
    Andersson, Rolf E
    Dimberg, Lena H
    Avenanthramides in Oats (Avena Sativa L.) and Structure-Activity Relationships2003In: Journal of Agricultural and Food Chemistry, ISSN 0021-8561, E-ISSN 1520-5118, Vol. 51, no 3, p. 594-600Article in journal (Refereed)
    Abstract [en]

    Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure−antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.

  • 20.
    Braunschweig, F.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Sörensen, J.
    von Bibra, H.
    Olsson, A.
    Ryden, L.
    Långström, B.
    Linde, C.
    Effects of long-term biventricular pacing on myocardial blood flow and oxygen consumption. A study using 11C-acetate-PET2003In: Am. J. Cardiol., Vol. 92, no 425, p. 95-99Article in journal (Refereed)
  • 21.
    Carlsson J, Bohl Kullberg E, Capala J, Sjöberg S, Edwards K, Gedda L.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Ligands liposomes and boron neutron capture therapy2003In: Journal of Neuro-Oncology, no 62, p. 47-59Article in journal (Other scientific)
  • 22.
    Casher, D.L
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Tsuji, H
    Katkevics, Sano A
    Katkevics, M
    Toshimitsu, A
    Tamao, K
    Kubota, M
    Kobayashi, T
    Ottosson, C.H
    David, D
    Michl, J.
    The Disilane Chromophore: Photoelectron an dElectronic Spectra of Hexaalkyldisilanes and 1, (n+,)-Disila[n.n.n]propellanes2003In: J Phys Chem A, no 107, p. 3559-3566Article in journal (Other scientific)
  • 23.
    Datta, Gopal K.
    et al.
    Uppsala Univ, Dept Organ Pharmaceut Chem, Biomed Ctr, Uppsala, Sweden..
    Vallin, Karl S. A.
    Uppsala Univ, Dept Organ Pharmaceut Chem, Biomed Ctr, Uppsala, Sweden..
    Larhed, Mats
    Uppsala Univ, Dept Organ Pharmaceut Chem, Biomed Ctr, Uppsala, Sweden..
    A rapid microwave protocol for Heck vinylation of aryl chlorides under air2003In: Molecular diversity, ISSN 1381-1991, E-ISSN 1573-501X, Vol. 7, no 2-4, p. 107-114Article in journal (Refereed)
    Abstract [en]

    In modern high-throughput chemistry, the overall workflow is a crucial factor and much work is devoted to speeding up the process of chemistry development. Since automated microwave-based synthesizers are known to streamline the compound production and to accelerate slow organic transformations, this technology was implemented for Heck reactions with sluggish aryl chlorides. Furthermore, homogeneous palladium-catalyzed Heck vinylations of aryl chlorides can be performed under air under optimized conditions. Based on this finding, controlled microwave heating was utilized to accelerate model reactions down to 30 min employing a mixture of ionic liquid and 1,4-dioxane as solvent.

  • 24. Dyson, P J
    et al.
    Laurenczy, G
    Ohlin, C A
    Vallance, J
    Welton, T
    Determination of hydrogen concentration in ionic liquids and the effect (or lack of) on rates of hydrogenation2003In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 19, p. 2418-2419Article in journal (Refereed)
    Abstract [en]

    The solubility of hydrogen and the corresponding Henry coefficients for 11 ionic liquids have been determined in situ at 100 atm H(2) pressure and are much lower than expected; attempts to correlate the solubility of hydrogen in the ionic liquids with the rate of reaction for the hydrogenation of benzene to cyclohexane in these solvents have been made.

  • 25.
    Edgren, E.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Enblad, P.
    Grenvik, Å.
    Lilja, A.
    Valind, S.
    Wiklund, L.
    Hedstrand, U.
    Stjernström, H.
    Persson, L., Pontén, U.
    Långström, B.
    Cerebral blood flow and metabolism after cardiopulmonary resucitation. A pathophysiologic and prognostic positron emission tomography pilot study.2003In: Resuscitation, Vol. 57, no 228, p. 161-170Article in journal (Refereed)
  • 26.
    Edin, Michaela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    On the mechanism of the unexpected facile formation of meso-diacetate products in enzymatic acetylation of alkanediols2003In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, p. 2216-2222Article in journal (Refereed)
  • 27.
    Ekegren, Jenny
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Roth, Peter
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Källström, Klas
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tarnai, Tibor
    Andersson, Pher
    Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Synthesis and evaluation of N,S-compounds as chiral ligands for transfer hydrogenation of acetophenone2003In: Org. Biomol. Chem, no 1, p. 358-366Article in journal (Refereed)
  • 28.
    Ekegren J.K, Roth P, Källström K, Tarnai T, Andersson P.G
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis and Evaluation of N,S-Ligands for Transfer Hydrogenation of Prochiral Ketones2003In: Org. Biomol. Chem., no 1, p. 358-Article in journal (Other scientific)
  • 29.
    El-Nahas, A
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Johansson, M
    Ottosson, H
    Reverse Si=C Bond Polarization as a Means for Stabilization of Silabenzenes: A Computational Investigation2003In: Organometallics, no 22, p. 5556-5566Article in journal (Refereed)
  • 30.
    Emtenäs, Hans
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria2003Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    New methods have been developed for the synthesis of bicyclic β-lactams and 2-pyridinones by combining acyl Meldrum’s acids and Δ2-thiazolines. The 2-pyridinones were synthesised both in solution using conventional heating or microwave assisted heating as well as by solid supported chemistry.

    The compounds (pilicides) were designed to interfere with the assembly of pili in uropathogenic E. coli by inhibiting the periplasmic chaperones. The affinity of the pilicides to the chaperones was investigated with surface plasmon resonance technique (Biacore) and with relaxation-edited 1H NMR spectroscopy experiments. Finally, the pilicides were investigated for their ability to inhibit pili formation in uropathogenic E. coli in a hemagglutination assay, where members of the 2-pyridinone family proved to be able to cause depiliation.

  • 31.
    Engler, H.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Blomquist, G.
    Nordberg, A.
    Wall, A.
    Estrada, S.
    Koivisto, P.
    Savitcheva, I.
    Sandell, J.
    Barletta, J.
    Antoni, Gunnar
    Bergström, M.
    Långström, B.
    PIB: a new tracer for imaging amyloid-b deposition in vivo. Comparison with FDG2003In: AMI, Madrid Spanien, 2003Conference paper (Other academic)
  • 32.
    Engler, H
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Lundberg, P.O
    Ekbom, K
    Nennesmo, I
    Nilsson, A
    Bergström, M
    Tsukada, H
    Hartvig, P
    Långström, B.
    Multitracer study with positron emission tomgraphy in Crutzfeldt-jakob disease2003In: Eur. J. Nucl. Med., no 30, p. 85-95Article in journal (Other scientific)
  • 33.
    Engman L, Al-Maharik N, MacNaughton M, Birmingham A, Powis G
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Thioredoxin Reductase and Cancer Cell Growth Inhibition by Organotellurium Antioxidants2003In: Anti-Cancer Drugs, no 14, p. 153-Article in journal (Other scientific)
  • 34.
    Engman, Lars
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Al-Maharik, Nawaf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    McNaughton, Michael
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Birmingham, A
    Uppsala University.
    Powis, G.
    Uppsala University.
    Thioredoxin Reductase and Cancer Cell Growth Inhibition by Organotellurium Compounds that could be Selectively Incorporated into Tumor Cells2003In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 11, no 23, p. 5091-5100Article in journal (Refereed)
    Abstract [en]

    The thioredoxins are small ubiquitous redox proteins with the conserved redox catalytic sequence-Trp-Cys-Gly-Pro-Cys-Lys, where the Cys residues undergo reversible NADPH dependent reduction by selenocysteine containing flavoprotein thioredoxin reductases. Thioredoxin expression is increased in several human primary cancers including lung, colon, cervix, liver, pancreatic, colorectal and squamous cell cancer. The thioredoxin/thioredoxin reductase pathway therefore provides an attractive target for cancer drug development. Organotellurium steroid, lipid, amino acid, nucleic base, and polyamine inhibitors were synthesized on the basis that they might be selectively or differentially incorporated into tumor cells. Some of the newly prepared classes of tellurium-based inhibitors (lipid-like compounds 3b and 3e, amino acid derivative 5b, nucleic base derivative 8b, and polyamine derivatives 14a and 14b) inhibited TrxR/Trx and cancer cell growth in culture with IC(50) values in the low micromolar range.

  • 35. Enquist, P A
    et al.
    Nilsson, P
    Larhed, M
    Ultrafast chemistry: Cobalt carbonyl-mediated synthesis of diaryl ketones under microwave irradiation2003In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 5, no 25, p. 4875-4878Article in journal (Refereed)
    Abstract [en]

    [GRAPHICS] By combining the advantages of metal activation, in situ carbon monoxide delivery, and microwave heating, benzophenones were efficiently synthesized in 6-10 s. These ultrafast carbonylation reactions occur under air by flash heating of aryl iodides in the presence of dicobalt octacarbonyl.

  • 36.
    Erdélyi, Máté
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase2003In: Journal of Organic Chemistry, Vol. 68, no 16, p. 6431-6434Article in journal (Refereed)
    Abstract [en]

    A microwave-enhanced, rapid, and efficient solidphase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15 to 25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.

  • 37.
    Eriksson L, Winberg K-J, Claro R.T, Sjöberg S.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Palladium-catalyzed Heck reactions of styrene derivatives and 2-I-p-carborane2003In: J. Org. ChemArticle in journal (Other scientific)
  • 38.
    Eriksson, P
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Engman, L
    An Antioxidant Composition Comprising Organic Tellurium Compound, Thiol Reducing Agent and Hindered Phenols2003In: PCT Int. Appl. WO, Vol. 03, no 52, p. 026-Article in journal (Refereed)
  • 39.
    Fagerlund, Amelie
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Shanks, David
    Sunnerheim, Kerstin
    Engman, Lars
    Frisell, Håkan
    Protective effects of synthetic and naturally occurring antioxidants in pulp products2003In: Nordic Pulp & Paper Research Journal, ISSN 0283-2631, E-ISSN 2000-0669, Vol. 18, p. 176-181Article in journal (Refereed)
    Abstract [en]

    Various types of natural and synthetic antioxidants when added to handsheets of pulp in low concentrations (0.2% weight%) could significantly reduce the emission of hexanal. The most efficient compounds caused a 90% reduction after eight weeks. Their capacity to inhibit brightness reversion was limited.

  • 40.
    Fagerlund, Amelie
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Shanks, David
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Sunnerheim, Kerstin
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Frisell, Håkan
    Protective Effects of Synthetic and Naturally Occurring Antioxidants in Pulp Products2003In: Nordic Pulp & Paper Research Journal, ISSN 0283-2631, E-ISSN 2000-0669, Vol. 18, no 2, p. 176-181Article in journal (Refereed)
    Abstract [en]

    Various types of natural and synthetic antioxidants when added to handsheets of pulp in low concentrations (0.2% weight%) could significantly reduce the emission of hexanal. The most efficient compounds caused a 90% reduction after eight weeks. Their capacity to inhibit brightness reversion was limited.

  • 41. Fang, Yao-ren
    et al.
    Gao, Ying
    Ryberg, Per
    Eriksson, Jonas
    Department of Organic Chemistry, Institute of Chemistry.
    Kolodziejska-Huben, Magdalena
    Dybala-Defratyka, Agnieszka
    Madhavan, S
    Danielsson, Rolf
    Paneth, Piotr
    Matsson, Olle
    Westaway, Kenneht Charles
    Experimental and Theoretical Multiple Kinetic Isotope Effects for an SN2 Reaction. An Attempt to Determine Transition-State Structure and the Ability of Theoretical Methods to Predict Experimental Kinetic Isotope Effects2003In: Chemistry European Journal, no 9, p. 2696-2709Article in journal (Refereed)
  • 42. Georgsson, J
    et al.
    Hallberg, A
    Larhed, M
    Rapid palladium-catalyzed synthesis of esters from aryl halides utilizing Mo(CO)(6) as a solid carbon monoxide source2003In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 5, no 4, p. 350-352Article in journal (Refereed)
  • 43.
    Guliashvili T, El-Sayed I, Fischer A, Ottosson H.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    The First Isolable 2-Silenolate2003In: Angewandte Chemie Int. Ed., no 42, p. 1640-1642Article in journal (Other scientific)
  • 44.
    Gustavsson, S.Å
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Kato, K.
    Långström, B.
    Purification of 11C-nitromethane for use in asymmetric aldol condensations2003In: J. Labe. Comp. Radiopharmaceuticals, Vol. 46, no 338, p. 1279-1285Article in journal (Refereed)
  • 45.
    Hartikka, A
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Modin, S
    Andersson, P.G
    Arvidsson, P.I.
    Cinchona Alkaloid derived Ligands in Catalytic Asymmetric Transfer Hydrogenation2003In: Org. Biomol. Chem., no 1, p. 2522-Article in journal (Refereed)
  • 46.
    Hellberg, Jonas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Remonen, Tommi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Allared, Fredrik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Slätt, Johnny
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Svensson, Mats
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Synthesis of 2,3-dihydrothieno[2,3-b]-1,4-dithiine, 2,3-dihydrothieno[3,2-b]-1,4-oxathiine, 2,3-dihydrothieno[2,3-b]-1,4-oxathiine and their transformation into corresponding end-capped oligomers.2003In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 14, p. 2199-2205Article in journal (Refereed)
    Abstract [en]

    Three new heterocyclic parent compds., 2,3-dihydrothieno[2,3-b][1,4]dithiine, 2,3-dihydrothieno[3,2-b][1,4]oxathiine, and 2,3-dihydrothieno[2,3-b][1,4]oxathiine, have been synthesized by acid-catalyzed transformations starting from 3-methoxythiophene. Two of the new compds. have been transformed to the corresponding end-capped dimeric, trimeric and tetrameric oligothiophenes. These oligomers show very stable cationic and dicationic states as judged by cyclic voltammetry, and their UV-Vis spectra are considerably red-shifted compared to previously synthesized end-capped oligomers. [on SciFinder(R)]

  • 47.
    Herlin, G.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Persson, B.
    Bergström, M.
    Långström, B.
    Aspelin, P.
    11C-harmine as a potential PET tracer for ductal pancreas cancer-in vitro studies2003In: Eur. Radiol., Vol. 13, no 459, p. 729-733Article in journal (Refereed)
  • 48. Jouve, Karine
    et al.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Oxidative cyclization of N-methyl- and N-benzoylpyridylthioureas. Preparation of new thiazolo[4,5-b] and [5,4-b]pyridine derivatives2003In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 40, no 2, p. 261-268Article in journal (Refereed)
  • 49. Kapoor, Mili
    et al.
    Srinivas, Honnappa
    Kandiah, Eaazhisai
    Gemma, Emiliano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ellgaard, Lars
    Oscarson, Stefan
    Helenius, Ari
    Surolia, Avadhesha
    Interactions of Substrate with Calreticulin, an Endoplasmic Reticulum Chaperone2003In: Journal of Biological Chemistry, ISSN 0021-9258, E-ISSN 1083-351X, Vol. 278, no 8, p. 6194–6200-Article in journal (Refereed)
  • 50.
    Karimi F, Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations2003In: Org. Biomol. Chem., no 1, p. 541-546Article in journal (Other scientific)
123 1 - 50 of 110
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