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  • 1.
    Andersson, Hans
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Gustafsson, Magnus
    Boström, Dan
    Umeå University, Faculty of Science and Technology, Department of Applied Physics and Electronics.
    Olsson, Roger
    Almqvist, Fredrik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    The Regio- and Stereoselective Synthesis of trans-2,3-Dihydropyridine N-oxides and Piperidines2009In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, no 18, p. 3288-3291Article in journal (Refereed)
    Abstract [en]

    No Abstract

  • 2.
    Berg, Lotta
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Niemiec, Moritz S.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Qian, Weixing
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Andersson, C. David
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Wittung-Stafshede, Pernilla
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Ekström, Fredrik
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Science and Technology, European CBRNE Center.
    Linusson, Anna
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Similar but Different: Thermodynamic and Structural Characterization of a Pair of Enantiomers Binding to Acetylcholinesterase2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 51, p. 12716-12720Article in journal (Refereed)
    Abstract [en]

    Take a closer look: Unexpectedly, a pair of enantiomeric ligands proved to have similar binding affinities for acetylcholinesterase. Further studies indicated that the enantiomers exhibit different thermodynamic profiles. Analyses of the noncovalent interactions in the protein-ligand complexes revealed that these differences are partly due to nonclassical hydrogen bonds between the ligands and aromatic side chains of the protein.

  • 3. Ceballos, Javier
    et al.
    Schwalfenberg, Melanie
    Karageorgis, George
    Reckzeh, Elena S.
    Sievers, Sonja
    Ostermann, Claude
    Pahl, Axel
    Sellstedt, Magnus
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Nowacki, Jessica
    Carnero Corrales, Marjorie A.
    Wilke, Julian
    Laraia, Luca
    Tschapalda, Kirsten
    Metz, Malte
    Sehr, Dominik A.
    Brand, Silke
    Winklhofer, Konstanze
    Janning, Petra
    Ziegler, Slava
    Waldmann, Herbert
    Synthesis of Indomorphan Pseudo-Natural Product Inhibitors of Glucose Transporters GLUT-1 and-32019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 47, p. 17016-17025Article in journal (Refereed)
    Abstract [en]

    Bioactive compound design based on natural product (NP) structure may be limited because of partial coverage of NP-like chemical space and biological target space. These limitations can be overcome by combining NP-centered strategies with fragment-based compound design through combination of NP-derived fragments to afford structurally unprecedented "pseudo-natural products" (pseudo-NPs). The design, synthesis, and biological evaluation of a collection of indomorphan pseudo-NPs that combine biosynthetically unrelated indole- and morphan-alkaloid fragments are described. Indomorphane derivative Glupin was identified as a potent inhibitor of glucose uptake by selectively targeting and upregulating glucose transporters GLUT-1 and GLUT-3. Glupin suppresses glycolysis, reduces the levels of glucose-derived metabolites, and attenuates the growth of various cancer cell lines. Our findings underscore the importance of dual GLUT-1 and GLUT-3 inhibition to efficiently suppress tumor cell growth and the cellular rescue mechanism, which counteracts glucose scarcity.

  • 4. Chen, Xi
    et al.
    Venkatachalapathy, Muthukumaran
    Dehmelt, Leif
    Wu, Yao-Wen
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR).
    Multidirectional Activity Control of Cellular Processes by a Versatile Chemo-optogenetic Approach2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 37, p. 11993-11997Article in journal (Refereed)
    Abstract [en]

    The spatiotemporal dynamics of proteins or organelles plays a vital role in controlling diverse cellular processes. However, acute control of activity at distinct locations within a cell is challenging. A versatile multidirectional activity control (MAC) approach is presented, which employs a photoactivatable system that may be dimerized upon chemical inducement. The system comprises second-generation SLF*-TMP (S*T) and photocaged NvocTMP-Cl dimerizers; where, SLF*-TMP features a synthetic ligand of the FKBP(F36V) binding protein, Nvoc is a caging group, and TMP is the antibiotic trimethoprim. Two MAC strategies are demonstrated to spatiotemporally control cellular signaling and intracellular cargo transport. The novel platform enables tunable, reversible, and rapid control of activity at multiple compartments in living cells.

  • 5. Chen, Xi
    et al.
    Venkatachalapathy, Muthukumaran
    Kamps, Dominic
    Weigel, Simone
    Kumar, Ravi
    Orlich, Michael
    Garrecht, Ruben
    Hirtz, Michael
    Niemeyer, Christof M.
    Wu, Yao-Wen
    Chemical Genomics Centre of the Max-Planck Society, Dortmund, Germany.
    Dehmelt, Leif
    “Molecular Activity Painting”: Switch-like, light-controlled perturbations inside living cells2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 21, p. 5916-5920Article in journal (Refereed)
    Abstract [en]

    Acute subcellular protein targeting is a powerful tool to study biological networks. However, signaling at the plasma membrane is highly dynamic, making it difficult to study in space and time. In particular, sustained local control of molecular function is challenging due to lateral diffusion of plasma membrane targeted molecules. Here we present “Molecular Activity Painting” (MAP), a novel technology which combines photoactivatable chemically induced dimerization (pCID) with immobilized artificial receptors. The immobilization of artificial receptors by surface-immobilized antibodies blocks lateral diffusion, enabling rapid and stable “painting” of signaling molecules and their activity at the plasma membrane with micrometer precision. Using this method, we show that painting of the RhoA-myosin activator GEF-H1 induces patterned acto-myosin contraction inside living cells.

  • 6.
    Chen, Xi
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Chemical Genomics Centre of the Max Planck Society, Dortmund, Germany; Max Planck Institute of Molecular Physiology, Dortmund, Germany.
    Wu, Yao-Wen
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Chemical Genomics Centre of the Max Planck Society, Dortmund, Germany; Max Planck Institute of Molecular Physiology, Dortmund, Germany.
    Tunable and Photoswitchable Chemically Induced Dimerization for Chemo-optogenetic Control of Protein and Organelle Positioning2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 23, p. 6796-6799Article in journal (Refereed)
    Abstract [en]

    The spatiotemporal dynamics of proteins and organelles play an important role in controlling diverse cellular processes. Optogenetic tools using photosensitive proteins and chemically induced dimerization (CID), which allow control of protein dimerization, have been used to elucidate the dynamics of biological systems and to dissect the complicated biological regulatory networks. However, the inherent limitations of current optogenetic and CID systems remain a significant challenge for the fine-tuning of cellular activity at precise times and locations. Herein, we present a novel chemo-optogenetic approach, photoswitchable chemically induced dimerization (psCID), for controlling cellular function by using blue light in a rapid and reversible manner. Moreover, psCID is tunable; that is, the dimerization and dedimerization degrees can be fine-tuned by applying different doses of illumination. Using this approach, we control the localization of proteins and positioning of organelles in live cells with high spatial (μm) and temporal (ms) precision.

  • 7.
    Cisneros, David A.
    et al.
    Biotechnologisches Zentrum, Technische Universität Dresden, Tatzberg 49, 01307 Dresden, Germany.
    Muller, Daniel J
    Daud, Sofian M
    Lakey, Jeremy H
    An approach to prepare membrane proteins for single-molecule imaging2006In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 45, no 20, p. 3252-3256Article in journal (Refereed)
  • 8.
    Deiana, Marco
    et al.
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Chand, Karam
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Jamroskovic, Jan
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Obi, Ikenna
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Chorell, Erik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Sabouri, Nasim
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    A Light‐up Logic Platform for Selective Recognition of Parallel G‐Quadruplex Structures via Disaggregation‐Induced Emission2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773Article in journal (Refereed)
    Abstract [en]

    The design of turn‐on dyes with optical signals sensitive to the formation of supramolecular structures provides fascinating and underexplored opportunities for G‐quadruplex (G4) DNA detection and characterization. Here, we show a new switching mechanism that relies on the recognition‐driven disaggregation (on‐signal) of an ultrabright coumarin‐quinazoline conjugate. The synthesized probe selectively lights‐up parallel G4 DNA structures via the disassembly of its supramolecular state, demonstrating outputs that are easily integrable into a label free molecular logic system. Finally, our molecule preferentially stains the G4‐rich nucleoli of cancer cells.

  • 9. Harley, Steven J.
    et al.
    Ohlin, C. Andre
    Johnson, Rene L.
    Panasci, Adele F.
    Casey, William H.
    The Pressure Dependence of Oxygen Isotope Exchange Rates Between Solution and Apical Oxygen Atoms on the [UO2(OH)(4)](2-) Ion2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 19, p. 4467-4469Article in journal (Refereed)
  • 10.
    Heller, Katharina
    et al.
    Center for Integrated Protein Science Munich, Technische Universität München, Department Chemistry, Lichtenbergstrasse 4, 85748 Garching, Germany.
    Ochtrop, Philipp
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Albers, Michael F.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Zauner, Florian B.
    Center for Integrated Protein Science Munich, Technische Universität München, Department Chemistry, Lichtenbergstrasse 4, 85748 Garching, Germany.
    Itzen, Aymelt
    Center for Integrated Protein Science Munich, Technische Universität München, Department Chemistry, Lichtenbergstrasse 4, 85748 Garching, Germany.
    Hedberg, Christian
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Dortmund, Germany.
    Covalent Protein Labeling by Enzymatic Phosphocholination2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 35, p. 10327-10330Article in journal (Refereed)
    Abstract [en]

    We present a new protein labeling method based on the covalent enzymatic phosphocholination of a specific octapeptide amino acid sequence in intact proteins. The bacterial enzyme AnkX from Legionella pneumophila has been established to transfer functional phosphocholine moieties from synthetically produced CDP-choline derivatives to N-termini, C-termini, and internal loop regions in proteins of interest. Furthermore, the covalent modification can be hydrolytically removed by the action of the Legionella enzyme Lem3. Only a short peptide sequence (eight amino acids) is required for efficient protein labeling and a small linker group (PEG-phosphocholine) is introduced to attach the conjugated cargo.

  • 11. Hernández-Torres, Gloria
    et al.
    Cipriano, Mariateresa
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    Hedén, Erika
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Clinical Neuroscience.
    Björklund, Emmelie
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    Canales, Ángeles
    Zian, Debora
    Feliú, Ana
    Mecha, Miriam
    Guaza, Carmen
    Fowler, Christopher J.
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    Ortega-Gutiérrez, Silvia
    López-Rodríguez, María L.
    A reversible and selective inhibitor of monoacylglycerol lipase ameliorates multiple sclerosis2014In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, no 50, p. 13765-13770Article in journal (Refereed)
    Abstract [en]

    Monoacylglycerol lipase (MAGL) is the enzyme responsible for the inactivation of the endocannabinoid 2-arachidonoylglycerol (2-AG). MAGL inhibitors show analgesic and tissue-protecting effects in several disease models. However, the few efficient and selective MAGL inhibitors described to date block the enzyme irreversibly, and this can lead to pharmacological tolerance. Hence, additional classes of MAGL inhibitors are needed to validate this enzyme as a therapeutic target. Here we report a potent, selective, and reversible MAGL inhibitor (IC50=0.18M) which is active in vivo and ameliorates the clinical progression of a multiple sclerosis (MS) mouse model without inducing undesirable CB1-mediated side effects. These results support the interest in MAGL as a target for the treatment of MS.

  • 12. Johnson, Rene L.
    et al.
    Ohlin, C. Andre
    Pellegrini, Kristi
    Burns, Peter C.
    Casey, William H.
    Dynamics of a Nanometer-Sized Uranyl Cluster in Solution2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 29, p. 7464-7467Article in journal (Refereed)
  • 13.
    Kuru, Erkin
    et al.
    Indiana University, Bloomington, USA.
    Hughes, H Velocity
    Indiana University, Bloomington, USA.
    Brown, Pamela J
    Indiana University, Bloomington, USA.
    Hall, Edward
    Indiana University, Bloomington, USA.
    Tekkam, Srinivas
    Indiana University, Bloomington, USA.
    Cava, Felipe
    Universidad Autonoma de Madrid, Campus de Cantoblanco, Madrid, Spain.
    de Pedro, Miguel A
    Universidad Autonoma de Madrid, Campus de Cantoblanco, Madrid, Spain.
    Brun, Yves V
    Indiana University, Bloomington, USA.
    VanNieuwenhze, Michael S
    Indiana University, Bloomington, USA.
    In Situ probing of newly synthesized peptidoglycan in live bacteria with fluorescent D-amino acids2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 50, p. 12519-12523Article in journal (Refereed)
    Abstract [en]

    Tracking a bug's life: Peptidoglycan (PG) of diverse bacteria is labeled by exploiting the tolerance of cells for incorporating different non-natural D-amino acids. These nontoxic D-amino acids preferably label the sites of active PG synthesis, thereby enabling fine spatiotemporal tracking of cell-wall dynamics in phylogenetically and morphologically diverse bacteria. HCC = 7-hydroxycoumarin, NBD = 7-nitrobenzofurazan, TAMRA = carboxytetramethylrhodamine.

  • 14. Laraia, Luca
    et al.
    Ohsawaa, Kosuke
    Konstantinidis, Georgios
    Robke, Lucas
    Wu, Yao-Wen
    Chemical Genomics Center of the Max Planck Society Otto-Hahn-Str.15, 44227 Dortmund.
    Kumar, Kamal
    Waldmann, Herbert
    Discovery of Novel Cinchona‐Alkaloid‐Inspired Oxazatwistane Autophagy Inhibitors2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 8, p. 2145-2150Article in journal (Refereed)
    Abstract [en]

    The cinchona alkaloids are a privileged class of natural products and are endowed with diverse bioactivities. However, for compounds with the closely‐related oxazatricyclo[4.4.0.0]decane (“oxazatwistane”) scaffold, which are accessible from cinchonidine and quinidine by means of ring distortion and modification, biological activity has not been identified. We report the synthesis of an oxazatwistane compound collection through employing state‐of‐the‐art C−H functionalization, and metal‐catalyzed cross‐coupling reactions as key late diversity‐generating steps. Exploration of oxazatwistane bioactivity in phenotypic assays monitoring different cellular processes revealed a novel class of autophagy inhibitors termed oxautins, which, in contrast to the guiding natural products, selectively inhibit autophagy by inhibiting both autophagosome biogenesis and autophagosome maturation.

  • 15. Manesiotis, Panagiotis
    et al.
    Hall, Andrew J.
    Courtois, Julien
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Irgum, Knut
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Sellergren, Börje
    An artificial riboflavin receptor prepared by a template analogue imprinting strategy2005In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 44, no 25, p. 3902-3906Article in journal (Refereed)
  • 16.
    Moodie, Lindon W. K.
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Hubert, Madlen
    Umeå University, Faculty of Medicine, Department of Integrative Medical Biology (IMB).
    Zhou, Xin
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Albers, Michael Franz
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Lundmark, Richard
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics. Umeå University, Faculty of Medicine, Department of Integrative Medical Biology (IMB).
    Wanrooij, Sjoerd
    Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
    Hedberg, Christian
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Photoactivated Colibactin Probes Induce Cellular DNA Damage2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 5, p. 1417-1421Article in journal (Refereed)
    Abstract [en]

    Colibactin is a small molecule produced by certain bacterial species of the human microbiota that harbour the pks genomic island. Pks(+) bacteria induce a genotoxic phenotype in eukaryotic cells and have been linked with colorectal cancer progression. Colibactin is produced in a benign, prodrug form which, prior to export, is enzymatically matured by the producing bacteria to its active form. Although the complete structure of colibactin has not been determined, key structural features have been described including an electrophilic cyclopropane motif, which is believed to alkylate DNA. To investigate the influence of the putative "warhead" and the prodrug strategy on genotoxicity, a series of photolabile colibactin probes were prepared that upon irradiation induced a pks(+) like phenotype in HeLa cells. Furthermore, results from DNA cross-linking and imaging studies of clickable analogues enforce the hypothesis that colibactin effects its genotoxicity by directly targeting DNA.

  • 17. Ohlin, C. Andre
    et al.
    Villa, Eric M.
    Fettinger, James C.
    Casey, William H.
    Distinctly Different Reactivities of Two Similar Polyoxoniobates with Hydrogen Peroxide2008In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 47, no 43, p. 8251-8254Article in journal (Refereed)
  • 18. Ohlin, C. André
    et al.
    Villa, Eric M.
    Fettinger, James C.
    Casey, William H.
    The [Ti(12)Nb(6)O(44)](10-) ion: A new type of polyoxometalate structure2008In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 47, no 30, p. 5634-5636Article in journal (Refereed)
  • 19. Orwick, Marcella C
    et al.
    Judge, Peter J
    Procek, Jan
    Lindholm, Ljubica
    Graziadei, Andrea
    Engel, Andreas
    Gröbner, Gerhard
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Watts, Anthony
    Detergent-free formation and physicochemical characterization of nanosized lipid-polymer complexes: lipodisq2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 19, p. 4653-4657Article in journal (Refereed)
    Abstract [en]

    Lipodisq particles are polymer-lipid complexes formed by detergent-free methods. Lipodisq particles containing dimyristoylphosphatidylcholine (DMPC) are characterized by increased lipid ordering compared to a DMPC dispersion. The styrene and maleic acid groups of the polymer interact with the DMPC lipid chains in bilayers, as well as lipid headgroups in the Lipodisq periphery.

  • 20. Pautler, Brent G.
    et al.
    Colla, Christopher A.
    Johnson, Rene L.
    Klavins, Peter
    Harley, Stephen J.
    Ohlin, C. Andre
    Sverjensky, Dimitri A.
    Walton, Jeffrey H.
    Casey, William H.
    A High-Pressure NMR Probe for Aqueous Geochemistry2014In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, no 37, p. 9788-9791Article in journal (Refereed)
    Abstract [en]

    A non-magnetic piston-cylinder pressure cell is presented for solution-state NMR spectroscopy at geochemical pressures. The probe has been calibrated up to 20kbar using insitu ruby fluorescence and allows for the measurement of pressure dependencies of a wide variety of NMR-active nuclei with as little as 10L of sample in a microcoil. Initial (BNMR)-B-11 spectroscopy of the H3BO3-catechol equilibria reveals a large pressure-driven exchange rate and a negative pressure-dependent activation volume, reflecting increased solvation and electrostriction upon boron-catecholate formation. The inexpensive probe design doubles the current pressure range available for solution NMR spectroscopy and is particularly important to advance the field of aqueous geochemistry.

  • 21. Perera, Ishanie Rangeeka
    et al.
    Daeneke, Torben
    Makuta, Satoshi
    Yu, Ze
    Tachibana, Yasuhiro
    Mishra, Amaresh
    Baeuerle, Peter
    Ohlin, C. André
    Bach, Udo
    Spiccia, Leone
    Application of the Tris(acetylacetonato)iron(III)/(II) Redox Couple in p-Type Dye-Sensitized Solar Cells2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 12, p. 3758-3762Article in journal (Refereed)
    Abstract [en]

    An electrolyte based on the tris(acetylacetonato)iron( III)/(II) redox couple ([Fe(acac)(3)](0/1)) was developed for p-type dye-sensitized solar cells (DSSCs). Introduction of a NiO blocking layer on the working electrode and the use of chenodeoxycholic acid in the electrolyte enhanced device performance by improving the photocurrent. Devices containing [Fe(acac)(3)](0/1-) and a perylene-thiophene-triphenylamine sensitizer (PMI-6T-TPA) have the highest reported short-circuit current (J(SC)=7.65 mA cm(-2)), and energy conversion efficiency (2.51%) for p-type DSSCs coupled with a fill factor of 0.51 and an open-circuit voltage V-OC=645 mV. Measurement of the kinetics of dye regeneration by the redox mediator revealed that the process is diffusion limited as the dye-regeneration rate constant (1.7 x 10(8) M-1 S-1) is very close to the maximum theoretical rate constant of 3.3 x 10(8) M-1 S-1. Consequently, a very high dye-regeneration yield (>99%) could be calculated for these devices.

  • 22.
    Pett, Christian
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Nasir, Waqas
    Sihlbom, Carina
    Olsson, Britt-Marie
    Caixeta, Vanessa
    Schorlemer, Manuel
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Zahedi, René P.
    Larson, Göran
    Nilsson, Jonas
    Westerlind, Ulrika
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Effective Assignment of α2,3/α2,6-Sialic Acid Isomers by LC-MS/MS-Based Glycoproteomics2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 30, p. 9320-9324Article in journal (Refereed)
    Abstract [en]

    Distinct structural changes of the α2,3/α2,6-sialic acid glycosidic linkages on glycoproteins are of importance in cancer biology, inflammatory diseases, and virus tropism. Current glycoproteomic methodologies are, however, not amenable toward high-throughput characterization of sialic acid isomers. To enable such assignments, a mass spectrometry method utilizing synthetic model glycopeptides for the analysis of oxonium ion intensity ratios was developed. This method was successfully applied in large-scale glycoproteomics, thus allowing the site-specific structural characterization of sialic acid isomers.

  • 23. Petzold, Daniel
    et al.
    Singh, Pardeep
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Almqvist, Fredrik
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    König, Burkhard
    Visible light mediated synthesis of β chloro ketones from aryl cyclopropanes2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, p. 8577-8580Article in journal (Refereed)
    Abstract [en]

    We report the visible light mediated synthesis of β chloro ketones from aryl cyclopropanes, oxygen, hydrochloric acid and nitric acid. The operationally simple and catalyst free method uses cheap standard lab reagents and displays a broad functional group tolerance. Moreover, scale up of the reaction and late stage functionalization of bioactive compounds is possible, providing the opportunity to utilize the cyclopropane ring as a masked β chloro ketone in a reaction sequence. We propose a light‐driven radical chain reaction initiated by the reaction of diluted hydrochloric and nitric acid producing small quantities of molecular chlorine. The mechanistic hypothesis is supported by 18O labelling and UV‐VIS experiments, cyclovoltammetry and several control reactions.

  • 24. Qian, Yong
    et al.
    Schuermann, Marc
    Janning, Petra
    Hedberg, Christian
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Waldmann, Herbert
    Activity-Based Proteome Profiling Probes Based on Woodward's Reagent K with Distinct Target Selectivity2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 27, p. 7766-7771Article in journal (Refereed)
    Abstract [en]

    Woodward's reagent K (WRK) is a reactive heterocyclic compound that has been employed in protein chemistry to covalently and unspecifically label proteins at nucleophilic amino acids, notably at histidine and cysteine. We have developed a panel of WRK-derived activity-based probes and show that surprisingly and unexpectedly, these probes are fairly selective for a few proteins in the human proteome. The WRK-derived probes show unique reactivity towards the catalytic N-terminal proline in the macrophage migration inhibitory factor (MIF) and can be used to label and, if equipped with a fluorophore, to image MIF activities in living cells.

  • 25. Robke, Lucas
    et al.
    Laraia, Luca
    Corrales, Marjorie A. Carnero
    Konstantinidis, Georgios
    Muroi, Makoto
    Richters, André
    Winzker, Michael
    Engbring, Tobias
    Tomassi, Stefano
    Watanabe, Nobumoto
    Osada, Hiroyuki
    Rauh, Daniel
    Waldmann, Herbert
    Wu, Yao-Wen
    Chemical Genomics Centreof the Max-Planck-Society Otto-Hahn-Strasse15, 44227 Dortmund.
    Engel, Julian
    Phenotypic Identification of a Novel Autophagy Inhibitor Chemotype Targeting Lipid Kinase VPS342017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 28, p. 8153-8157Article in journal (Refereed)
    Abstract [en]

    Autophagy is a critical regulator of cellular homeostasis and metabolism. Interference with this process is considered a new approach for the treatment of disease, in particular cancer and neurological disorders. Therefore, novel small‐molecule autophagy modulators are in high demand. We describe the discovery of autophinib, a potent autophagy inhibitor with a novel chemotype. Autophinib was identified by means of a phenotypic assay monitoring the formation of autophagy‐induced puncta, indicating accumulation of the lipidated cytosolic protein LC3 on the autophagosomal membrane. Target identification and validation revealed that autophinib inhibits autophagy induced by starvation or rapamycin by targeting the lipid kinase VPS34.

  • 26. Shen, Hangjia
    et al.
    Gracia-Espino, Eduardo
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Ma, Jingyuan
    Zang, Ketao
    Luo, Jun
    Wang, Le
    Gao, Sanshuang
    Mamat, Xamxikamar
    Hu, Guangzhi
    Umeå University, Faculty of Science and Technology, Department of Physics. Key Laboratory of Chemistry of Plant Resources in Arid Regions State Key Laboratory Basis of Xinjiang indigenous medicinal plants resource utilization Xinjiang Technical Institute of Physics and Chemistry Chinese Academy of Sciences.
    Wågberg, Thomas
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Guo, Shaojun
    Synergistic Effects between Atomically Dispersed Fe-N-C and C-S-C for the Oxygen Reduction Reaction in Acidic Media2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 44, p. 13800-13804Article in journal (Refereed)
    Abstract [en]

    Various advanced catalysts based on sulfur-doped Fe/N/C materials have recently been designed for the oxygen reduction reaction (ORR); however, the enhanced activity is still controversial and usually attributed to differences in the surface area, improved conductivity, or uncertain synergistic effects. Herein, a sulfur-doped Fe/N/C catalyst (denoted as Fe/SNC) was obtained by a template-sacrificing method. The incorporated sulfur gives a thiophene-like structure (C-S-C), reduces the electron localization around the Fe centers, improves the interaction with oxygenated species, and therefore facilitates the complete 4e(-) ORR in acidic solution. Owing to these synergistic effects, the Fe/SNC catalyst exhibits much better ORR activity than the sulfur-free variant (Fe/NC) in 0.5m H2SO4.

  • 27. Shuaishuai, Wang
    et al.
    Qing, Zhang
    CongCong, Chen
    Yuxi, Guo
    Reddy, Gadi Madhusudhan
    Jin, Yu
    Ulrika, Westerlind
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Yunpeng, Liu
    Xuefeng, Cao
    G., Wang Peng
    Lei, Li
    Facile Chemoenzymatic Synthesis of O-Mannosyl Glycans2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 30, p. 9268-9273Article in journal (Refereed)
    Abstract [en]

    Abstract O?Mannosylation is a vital protein modification involved in brain and muscle development whereas the biological relevance of O-mannosyl glycans has remained largely unknown owing to the lack of structurally defined glycoforms. An efficient scaffold synthesis/enzymatic extension (SSEE) strategy was developed to prepare such structures by combining gram-scale convergent chemical syntheses of three scaffolds and strictly controlled sequential enzymatic extension catalyzed by glycosyltransferases. In total, 45 O-mannosyl glycans were obtained, covering the majority of identified mammalian structures. Subsequent glycan microarray analysis revealed fine specificities of glycan-binding proteins and specific antisera.

  • 28. Smit, Cornelis
    et al.
    Blümer, Julia
    Eerland, Martijn F
    Albers, Michael F
    Max-Planck-Institut für molekulare Physiologie Abt. Chemische Biologie.
    Müller, Matthias P
    Goody, Roger S
    Itzen, Aymelt
    Hedberg, Christian
    Efficient synthesis and applications of peptides containing adenylylated tyrosine residues2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 39, p. 9200-9204Article in journal (Refereed)
  • 29. Spillane, Samuel
    et al.
    Sharma, Rupali
    Zavras, Athanasios
    Mulder, Roger
    Ohlin, C. Andre
    Umeå University, Faculty of Science and Technology, Department of Chemistry. School of Chemistry, Monash University Victoria, Australia.
    Goerigk, Lars
    O’Hair, Richard A. J.
    Ritchie, Chris
    Non-aqueous microwave-assisted syntheses of deca- and hexa-molybdovanadates2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, p. 8568-8572Article in journal (Refereed)
    Abstract [en]

    We report a new approach for the synthesis of heterohexa- and heterodecametalates via the use of non-aqueous, microwave-assisted reaction conditions. The two novel molybdovanadates have been isolated and characterized in the solid and solution states using single-crystal X-ray diffraction, FT-IR, UV/Vis, multinuclear NMR spectroscopy, and ESI-MS. The relative stabilities of the possible structural isomers were probed using dispersion-corrected DFT calculations for both polyoxometalate systems.

  • 30.
    Spjut, Sara
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR). Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    Qian, Weixing
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR). Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    Bauer, Johannes
    Storm, Rickard
    Umeå University, Faculty of Medicine, Department of Clinical Microbiology, Virology. Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    Frängsmyr, Lars
    Umeå University, Faculty of Medicine, Department of Clinical Microbiology, Virology. Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    Stehle, Thilo
    Arnberg, Niklas
    Umeå University, Faculty of Medicine, Department of Clinical Microbiology, Virology. Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    Elofsson, Mikael
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR). Umeå University, Faculty of Medicine, Molecular Infection Medicine Sweden (MIMS).
    A Potent Trivalent Sialic Acid Inhibitor of Adenovirus Type 37 Infection of Human Corneal Cells2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 29, p. 6519-6521Article in journal (Refereed)
  • 31.
    Sun, Jinhua
    et al.
    Umeå University, Faculty of Science and Technology, Department of Physics. Department of Industrial and Materials Science, Chalmers Tekniska Högskola 41296 Göteborg (Sweden).
    Iakunkov, Artem
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Baburin, Igor A.
    Joseph, Boby
    Palermo, Vincenzo
    Talyzin, Aleksandr V.
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Covalent Organic Framework (COF-1) under High Pressure2020In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 59, no 3, p. 1087-1092Article in journal (Refereed)
    Abstract [en]

    COF‐1 has a structure with rigid 2D layers composed of benzene and B3O3 rings and weak van der Waals bonding between the layers. The as‐synthesized COF‐1 structure contains pores occupied by solvent molecules. A high surface area empty‐pore structure is obtained after vacuum annealing. High‐pressure XRD and Raman experiments with mesitylene‐filled (COF‐1‐M) and empty‐pore COF‐1 demonstrate partial amorphization and collapse of the framework structure above 12–15 GPa. The ambient pressure structure of COF‐1‐M can be reversibly recovered after compression up to 10–15 GPa. Remarkable stability of highly porous COF‐1 structure at pressures at least up to 10 GPa is found even for the empty‐pore structure. The bulk modulus of the COF‐1 structure (11.2(5) GPa) and linear incompressibilities (k[100]=111(5) GPa, k[001]=15.0(5) GPa) were evaluated from the analysis of XRD data and cross‐checked against first‐principles calculations.

  • 32.
    Sun, Jinhua
    et al.
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Klechikov, Alexey
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Moise, Calin
    Prodana, Mariana
    Enachescu, Marius
    Talyzin, Alexandr
    Umeå University, Faculty of Science and Technology, Department of Physics.
    A Molecular Pillar Approach To Grow Vertical Covalent Organic Framework Nanosheets on Graphene: Hybrid Materials for Energy Storage2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 4, p. 1034-1038Article in journal (Refereed)
    Abstract [en]

    Hybrid 2D–2D materials composed of perpendicularly oriented covalent organic frameworks (COFs) and graphene were prepared and tested for energy storage applications. Diboronic acid molecules covalently attached to graphene oxide (GO) were used as nucleation sites for directing vertical growth of COF-1 nanosheets (v-COF-GO). The hybrid material has a forest of COF-1 nanosheets with a thickness of 3 to 15 nm in edge-on orientation relative to GO. The reaction performed without molecular pillars resulted in uncontrollable growth of thick COF-1 platelets parallel to the surface of GO. The v-COF-GO was converted into a conductive carbon material preserving the nanostructure of precursor with ultrathin porous carbon nanosheets grafted to graphene in edge-on orientation. It was demonstrated as a high-performance electrode material for supercapacitors. The molecular pillar approach can be used for preparation of many other 2D-2D materials with control of their relative orientation.

  • 33.
    Talyzin, Alexandr V.
    et al.
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Luzan, Serhiy M.
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Anoshkin, Ilya V.
    NanoMaterials Group, Department of Applied Physics and Center for New Materials, Aalto University, Aalto, Espoo, Finland.
    Nasibulin, Albert G.
    NanoMaterials Group, Department of Applied Physics and Center for New Materials, Aalto University, Aalto, Espoo, Finland.
    Jiang, Hua
    NanoMaterials Group, Department of Applied Physics and Center for New Materials, Aalto University, Aalto, Espoo, Finland.
    Kauppinen, Esko I.
    NanoMaterials Group, Department of Applied Physics and Center for New Materials, Aalto University, Aalto, Espoo, Finland.
    Hydrogen-driven collapse of C60 inside single-walled Carbon Nanotubes2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 18, p. 4435-4439Article in journal (Refereed)
  • 34.
    Trillo, Paz
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Slagbrand, Tove
    Adolfsson, Hans
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Straightforward alpha-Amino Nitrile Synthesis Through Mo(CO)(6)-Catalyzed Reductive Functionalization of Carboxamides2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 38, p. 12347-12351Article in journal (Refereed)
    Abstract [en]

    The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)(6) together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of alpha-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of alpha-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.

  • 35. van Poll, Maaike L
    et al.
    Zhou, Feng
    Ramstedt, Madeleine
    Department of Chemistry, University of Cambridge.
    Hu, Litian
    Huck, Wilhelm T S
    A self-assembly approach to chemical micropatterning of poly(dimethylsiloxane)2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, no 35, p. 6634-7Article in journal (Refereed)
    Abstract [en]

    The surface of a silicone elastomer (poly(dimethylsiloxane); PDMS) can be selectively modified through minimization of interfacial free energy and self-assembly of functional molecules at the surface by mirroring the distribution of template surface energies (see scheme for formation of POEGMA brushes; SAM=self-assembled monolayer, bipy=2,2′-bipyridyl, POEGMA=poly[oligo(ethylene glycol) methacrylate]).

  • 36. Villa, Eric M.
    et al.
    Ohlin, C. Andre
    Balogh, Edina
    Anderson, Travis M.
    Nyman, May D.
    Casey, William H.
    Reaction dynamics of the decaniobate ion [HxNb10O28]((6-x)-) in water2008In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 47, no 26, p. 4844-4846Article in journal (Refereed)
  • 37.
    You, Shujie
    et al.
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Kunz, Daniel
    Stöter, Matthias
    Kalo, Hussein
    Putz, Bernd
    Breu, Josef
    Talyzin, Alexandr
    Umeå University, Faculty of Science and Technology, Department of Physics.
    Pressure-induced water insertion in synthetic clays2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 14, p. 3891-3895Article in journal (Refereed)
1 - 37 of 37
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