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  • 1.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Transition metal-catalyzed epoxidation of alkenes2010In: Modern Oxidation Methods / [ed] Jan-Erling Bäckvall, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 2, p. 37-84Chapter in book (Other academic)
  • 2.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zaitsev, Alexey
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ryberg, Per
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric transfer hydrogenation of ketones catalyzed by amino acid derived rhodium complexes: on the origin of enantioselectivity and enantioswitchability: Corrigendum to vol 15(2009) 42, pp. 11197-2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 35, p. 10610-10610Article in journal (Refereed)
  • 3.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ryberg, Per
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nordin, Mikael
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanistic investigation of enantioswitchable catalysts for asymmetric transfer hydrogenation2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco , CA, United States, March 21-25, 2010, Washington: American Chemical Society , 2010Conference paper (Other academic)
  • 4.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lundberg, Helena
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature2010In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 12, no 9, p. 1628-1633Article in journal (Refereed)
    Abstract [en]

    An environmentally benign method for the transformation of allylic alcohols into carbonyl compounds is described. Using [Rh(COD(CH3CN)(2)]BF4 (2) in combination with 1,3,5-triaza-7-phosphaadamantane (PTA, 1) as the catalytic system in water results in a very fast redox isomerisation of a variety of secondary allylic alcohols at ambient temperature. Also, some primary allylic alcohols can be isomerised into the corresponding aldehydes. The active complex, which in some cases can be used in catalyst loadings as low as 0.5 mol%, is formed in situ from commercially available reagents. Based on deuterium labelling studies, a tentative mechanism involving metal-enone intermediates is presented.

  • 5.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalysed coupling of allylic, homoallylic, and bishomoallylic alcohols with aldehydes and N-tosylimines2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, American Chemical Society , 2010Conference paper (Other academic)
  • 6. Ai, Yue-Jie
    et al.
    Liao, Rong-zhen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chen, Shu-feng
    Luo, Yi
    Fang, Wei-Hai
    Theoretical Studies on Photoisomerizations of (6-4) and Dewar Photolesions in DNA2010In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 114, no 44, p. 14096-14102Article in journal (Refereed)
    Abstract [en]

    The (6-4) photoproduct ((6-4) PP) is one of the main lesions in UV-induced DNA damage. The (6-4) PP and its valence isomer Dewar photoproduct (Dewar PP) can have a great threat of mutation and cancer but gained much less attention to date. In this study, with density functional theory (DFT) and the complete active space self-consistent field (CASSCF) methods, the photoisomerization processes between the (6-4) PP and the Dewar PP in the gas phase, the aqueous solution, and the photolyase have been carefully examined. Noticeably, the solvent effect is treated with the CASPT2//CASSCF/Amber (QM/MM) method. Our calculations show that the conical intersection (Cl) points play a crucial role in the photoisomerization reaction between the (6-4) PP and the Dewar PP in the gas and the aqueous solution. The ultrafast internal conversion between the S-2 ((1)pi pi*) and the So states via a distorted intersection point is found to be responsible for the formation of the Dewar PP lesion at 313 nm, as observed experimentally. For the reversed isomeric process, two channels involving the "dark" excited states have been identified. In addition to the above passages, in the photolyase, a new electron-injection isomerization process as an efficient way for the photorepair of the Dewar PP is revealed.

  • 7.
    Buitrago, Elina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Transition metal catalyzed reduction of ketones2010Licentiate thesis, comprehensive summary (Other academic)
  • 8.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Modern Oxidation Methods2010Collection (editor) (Other academic)
  • 9.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Preface2010In: Topics in catalysis, ISSN 1022-5528, E-ISSN 1572-9028, Vol. 53, no 13-14, p. 831-831Article in journal (Refereed)
  • 10.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective oxidation of amines and sulfides2010In: Modern Oxidation Methods / [ed] Jan-Erling Bäckvall, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 2, p. 277-313Chapter in book (Other academic)
  • 11. Chowdhury, Sugata
    et al.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Russo, Nino
    Sicilia, Emilia
    Mechanistic investigation of the hydrogenation of O2 by a transfer hydrogenation catalyst2010In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 132, no 12, p. 4178-4190Article in journal (Refereed)
  • 12.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Short synthesis of a benzyl ether protected building block for the synthesis of carbocyclic galactopyranose mimics2010In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 345, no 8, p. 1056-1060Article in journal (Refereed)
  • 13.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ramstadius, Clinton
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Akhtar, Tashfeen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Goldstein, Irwin J
    Department of Biological Chemistry, University of Michigan Medical School, Ann Arbor, MI .
    Winter, Harry C
    Department of Biological Chemistry, University of Michigan Medical School, Ann Arbor, MI .
    Non-glycosidically linked pseudodisaccharides: thioethers, sulfoxides, sulfones, ethers, selenoethers, and their binding to lectins2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 10, p. 1951-1970Article in journal (Refereed)
    Abstract [en]

    Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxygen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such compounds is described

  • 14.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric bifunctional catalysis using heterobimetallic and multimetallic systems in enantioselective conjugate additions2010In: Catalytic Asymmetric Conjugate Reactions / [ed] Armando Córdova, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 1, p. 169-190Chapter in book (Other academic)
  • 15.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic Asymmetric Conjugate Reactions2010Collection (editor) (Other academic)
  • 16.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ullah, Farman
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic asymmetric transformation (DYKAT) by combination of amine and transition metal cascade catalysis2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, Washington, D C: American Chemical Society , 2010Conference paper (Other academic)
  • 17.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzik, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 2, p. 234-237Article in journal (Refereed)
    Abstract [en]

    A highly enantioselective catalytic route to carbamate- and benzoate-protected beta-amino aldehydes and beta-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and alpha-amido sulfones gives the corresponding beta-amino compounds with up to 95:5 dr and 97-99%

  • 18.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhang, Qiong
    Leijonmarck, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Organocatalytic enantioselective aziridination of α-substituted α,β-unsaturated aldehydes: asymmetric synthesis ot terminal aziridines2010In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 352, no 18, p. 3201-3207Article in journal (Refereed)
    Abstract [en]

    The first example of a highly enantioselective organocatalytic aziridination of α-substituted α,β-unsaturated aldehydes is presented. The reaction is catalyzed by simple chiral amines and gives access to highly functional terminal azirdines containing an α-tertiary amine stereocenter in high yields and enantiomeric ratios (95.5:4.5–98:2).

  • 19.
    Deska, Jan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    del Pozo Ochoa, Carolina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chemoenzymatic dynamic kinetic resolution of axially chiral allenes2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 15, p. 4447-4451Article in journal (Refereed)
    Abstract [en]

    Dimeric palladium bromide complexes bearing monodentate N-heterocyclic carbene ligands have been identified as efficient catalysts for the chemoselective racemization of axially chiral allenyl alcohols. In combination with porcine pancreatic lipase as biocatalyst, a dynamic kinetic resolution has been developed, giving access to optically active allenes in good yield and high enantiomeric purity (

  • 20.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schyman, Patric
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kullberg, Martin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly enantioselective organocatalytic addition of aldehydes to acylimines: Asymmetric syntheses of the paclitaxel and docetaxel side-chains and their analogs2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, Washington, D C: American Chemical Society , 2010Conference paper (Other academic)
  • 21.
    Engström, Karin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Protein engineering of enzymes for improved enantioselectivity and application of engineered enzymes in organic synthesis2010Licentiate thesis, comprehensive summary (Other academic)
  • 22.
    Engström, Karin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nyhlén, Jonas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sandström, Anders G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Directed evolution of an enantioselective lipase with broad substrate scope for hydrolysis of α-substituted esters2010In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 132, no 20, p. 7038-7042Article in journal (Refereed)
    Abstract [en]

    A variant of Candida antarctica lipase A (CalA) was developed for the hydrolysis of α-substituted p-nitrophenyl esters by directed evolution. The E values of this variant for 7 different esters was 45−276, which is a large improvement compared to 2−20 for the wild type. The broad substrate scope of this enzyme variant is of synthetic use, and hydrolysis of the tested substrates proceeded with an enantiomeric excess between 95−99%. A 30-fold increase in activity was also observed for most substrates. The developed enzyme variant shows (R)-selectivity, which is reversed compared to the wild type that is (S)-selective for most substrates.

  • 23.
    Engström, Karin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nyhlén, Jonas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sandström, Anders G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective Kinetic Resolution of p-Nitrophenyl 2-Phenylpropanoate by a Variant of Candida antarctica Lipase A Developed by Directed Evolution2010In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 132, no 20, p. 7038-7042Article in journal (Refereed)
    Abstract [en]

    A variant of Candida antarctica lipase A (CalA) was developed for the hydrolysis of α-substituted p-nitrophenyl esters by directed evolution. The E values of this variant for 7 different esters was 45−276, which is a large improvement compared to 2−20 for the wild type. The broad substrate scope of this enzyme variant is of synthetic use, and hydrolysis of the tested substrates proceeded with an enantiomeric excess between 95−99%. A 30-fold increase in activity was also observed for most substrates. The developed enzyme variant shows (R)-selectivity, which is reversed compared to the wild type that is (S)-selective for most substrates.

  • 24. Eriksson, Kristofer L. E.
    et al.
    Chow, Winnie W. Y.
    Puglia, Carla
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Göthelid, Emmanuelle
    Oscarsson, Sven
    Performance of a biomimetic oxidation catalyst immobilized on silicon wafers: comparison with its gold congener2010In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 26, no 21, p. 16349-16354Article in journal (Refereed)
    Abstract [en]

    With the aim of extending the usefulness of an existing biomimetic catalytic system, cobalt porphyrin catalytic units with thiol linkers were heterogenized via chemical grafting to silicon wafers and utilized for the catalytic oxidation of hydroquinone to p-benzoquinone. Atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS) were used to analyze the morphology and composition of the heterogeneous catalyst. The results of the catalytic oxidation of hydroquinone obtained with porphyrins grafted on silicon were compared with those obtained earlier with the same catalyst in homogeneous phase and immobilized on gold. It was found that the catalysis could run over 400 h, without showing any sign of deactivation. The measured catalytic activity is at least 10 times higher than that measured under homogeneous conditions, but also 10 times lower than that observed with the catalytic unit immobilized on gold. The reasons of this discrepancy are discussed in term of substrate influence and overlayer organization. The silicon-immobilized catalyst has potential as an advanced functional material with applications in oxidative heterogeneous catalysis of organic reactions, as it combines long-term relatively high activity with low cost.

  • 25. Fourniere, Viviane
    et al.
    Skantz, Linnea
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sajtos, Ferenc
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Lahmann, Martina
    Synthesis of the Lewis b pentasaccharide and a HSA-conjugate thereof2010In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 39, p. 7850-7855Article in journal (Refereed)
    Abstract [en]

    Helicobacter pylori, a gastric pathogen, binds to various blood group antigens, including the Lewis types, present in the gastric tissue and a relation between the presentation of the ligands and the overall strength of binding has been assumed. Synthetic Lewis b tetra- and hexasaccharide conjugates are available but not the analogous pentasaccharide. An efficient synthesis of the amino spacer equipped Lewis b pentasaccharide, 3-aminopropyl alpha-L-fucopyranosyl-(1 -> 2)-beta-D-galactopyranosyl-(1 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 3)-beta-D-galactopyranoside, is presented to enable further investigation of the carbohydrate recognition process of H. pylori.

  • 26.
    Fournière, Viviane
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of non-glycosidically linked selenoether pseudodisaccharides2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 16, p. 2127-2129Article in journal (Refereed)
    Abstract [en]

    Non-glycosidically linked disaccharide mimetics with a selenoether functionality linking the two monosaccharide residues have been synthesised. Protected Glc(Se3–3)Glc, Glc(Se3–6)Glc and Glc(Se3–6)Man structures were obtained. Selenium was introduced by displacement of carbohydrate sulfonates with a selenobenzoate anion. Conversion into diselenides by methanolysis of the benzoate and aerial oxidation was followed by reduction of the diselenides to selenolates, and in situ displacement of a second carbohydrate sulfonate in an SN2 reaction to give selenoethers. Glc(Se3–3)Glc and Glc(Se3–6)Glc were also obtained in deprotected form.

  • 27.
    Frigell, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of O-linked Carbasugar Analogues of Galactofuranosides and N-linked Neodisaccharides2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In this thesis, carbohydrate mimicry is investigated through the syntheses of carbohydrate analogues and evaluation of their inhibitory effects on carbohydrate-processing enzymes.

    Galactofuranosides are interesting structures because they are common motifs in pathogenic microorganisms but not found in mammals. M.tuberculosis, responsible for the disease tuberculosis, has a cell wall containing a repeating unit of alternating (1→5)- and (1→6)-linked β-D-galactofuranosyl residues. Synthetic inhibitors of the enzymes involved in the biosynthesis of the cell wall could find great therapeutic use.

    The first part of this thesis describes the first synthesis of the hydrolytically stable carbasugar analogue of galactofuranose, 4a-carba-β-D-Galf, and the synthetic work of synthesising β-linked pseudodisaccharides containing carba-Galf, which were tested for glycosyltransferease inhibitory activity. The pseudodisaccharide carba-Galf-(β1→5)-carba-Galf was found to be a moderate inhibitor of the glycosyltransferase GlfT2 of M.tuberculosis. The thesis also describes how a general method towards biologically relevant α-linked carba-Galf ethers was developed.

    The final part of this thesis is focussed on the formation of nitrogen-linked monosaccharides without the participation of the anomeric centre. Such a mode of coupling is called tail-to-tail neodisaccharide formation. The couplings of carbohydrate derivatives via the Mitsunobu reaction are successfully reported herein. The method describes the key introduction of an allylic alcohol in the electrophile and the subsequent functionalisation of the alkene to obtain the neodisaccharide. Two synthesised neodisaccharides presented in this thesis have been sent to be tested for glycosidase inhibitory activity.

  • 28.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carbasugar analogues of galactofuranosides: alpha-O-linked derivatives2010In: BEILSTEIN J ORG CHEM, ISSN 1860-5397, Vol. 6, p. 1127-1131Article in journal (Refereed)
    Abstract [en]

    Using an indirect method, we have synthesised alpha-linked carbasugar analogues of galactofuranosides for the first time. Ring opening of a beta-talo configured carbasugar 1,2-epoxide by alcohol nucleophiles under Lewis acidic conditions proceeded with very good regioselectivity to give alpha-talo configured C1-substituted ethers with a free OH-group at the C2 position. Inversion of configuration at C2 by an oxidation-reduction sequence gave the alpha-galacto configured carbahexofuranose C1 ethers. A carbadisaccharide corresponding to the Galf(alpha 1 -> 3)Manp substructure from Apodus deciduus galactomannan was synthesised to exemplify the method.

  • 29.
    Gao, Weiming
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Åkermark, Torbjörn
    Li, Mingrun
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Sun, Licheng
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Attachment of a hydrogen-bonding carboxylate side chain to an [FeFe]-hydrogenase model complex: Influence on the catalytic mechanism2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 8, p. 2537-2546Article in journal (Refereed)
    Abstract [en]

    Azapropanedithiolate (adt)-bridged model complexes of [FeFe]-hydrogenase bearing a carboxylic acid functionality have been designed with the aim of decreasing the potential for reduction of protons to hydrogen. Protonation of the bisphosphine complexes 46 has been studied by in situ IR and NMR spectroscopy, which revealed that protonation with triflic acid most likely takes place first at the N-bridge for complex 4 but at the FeFe bond for complexes 5 and 6. Using an excess of acid, the diprotonated species could also be observed, but none of the protonated species was sufficiently stable to be isolated in a pure state. Electrochemical studies have provided an insight into the catalytic mechanisms under strongly acidic conditions, and have also shown that complexes 3 and 6 are electro-active in aqueous solution even in the absence of acid, presumably due to hydrogen bonding. Hydrogen evolution, driven by visible light, has been observed for three-component systems consisting of [Ru(bpy)3]2+, complex 1, 2, or 3, and ascorbic acid in CH3CN/D2O solution by on-line mass spectrometry.

  • 30.
    Georgieva, Polina
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Quantum chemical modeling of enzymatic reactions: The Case of histone lysine methyltransferase2010In: Journal of Computational Chemistry, ISSN 0192-8651, E-ISSN 1096-987X, Vol. 31, no 8, p. 1707-1714Article in journal (Refereed)
    Abstract [en]

    Quantum chemical cluster models of enzyme active sites are today an important and powerful tool in the study of various aspects of enzymatic reactivity. This methodology has been applied to a wide spectrum of reactions and many important mechanistic problems have been solved. Herein, we report a systematic study of the reaction mechanism of the histone lysine methyltransferase (HKMT) SET7/9 enzyme, which catalyzes the methylation of the N-terminal histone tail of the chromatin structure. In this study, HKMT SET7/9 serves as a representative case to examine the modeling approach for the important class of methyl transfer enzymes. Active site models of different sizes are used to evaluate the methodology. In particular, the dependence of the calculated energies on the model size, the influence of the dielectric medium, and the particular choice of the dielectric constant are discussed. In addition, we examine the validity of some technical aspects, such as geometry optimization in solvent or with a large basis set, and the use of different density functional methods.

  • 31. Godefroid, Marie
    et al.
    Svensson, Mona V
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cambier, Pierre
    Uzureau, Sophie
    Mirabella, Aurélie
    De Bolle, Xavier
    Van Cutsem, Pierre
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Letesson, Jean-Jacques
    Brucella melitensis 16M produces a mannan and other extracellular matrix components typical of a biofilm2010In: FEMS Immunology and Medical Microbiology, ISSN 0928-8244, E-ISSN 1574-695X, Vol. 59, no 3, p. 364-377Article in journal (Refereed)
  • 32.
    Hamark, Christoffer
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Landström, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-D-glucopyranoside2010In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. E66, p. o3250-o3251Article in journal (Refereed)
    Abstract [en]

    In the title compound, C30H31NO6S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thioethyl group has the exo-anomeric conformation. The hydroxy group forms an intermolecular hydrogen bond to the O atom in the sugar ring, generating [100] chains. There are four close - contacts with centroid-centroid distances less than 4.0 Å, all with dihedral angles between the interacting systems of only 8°, supporting energetically favourable stacking interactions

  • 33.
    Hamark, Christoffer
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Landström, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ethyl 4,6-O-benzylidene-2-deoxy-N-phthalimido-1-thio-β-D-glucopyranoside2010In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. E66, p. o3249-Article in journal (Refereed)
  • 34.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis and applications of diaryliodonium salts2010Licentiate thesis, comprehensive summary (Other academic)
  • 35.
    Jalalian, Nazli
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Design and asymmetric synthesis of chiral diaryliodonium salts2010In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 31, p. 5793-5800Article in journal (Refereed)
    Abstract [en]

    The application of chiral hypervalent iodine reagents in asymmetric synthesis is highly desirable, as the reagents are metal-free, environmentally benign and employed under mild conditions. Three chiral diaryliodonium salts have been designed to provide chemoselectivity and asymmetric induction in asymmetric alpha-phenylation of carbonyl compounds. The synthetic routes to the selected targets are detailed herein, together with a structural investigation into the diastereoselectivity of the alkylation process.

  • 36.
    Johnston, Eric V
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective synthesis of (R)-bufuralol via dynamic kinetic resolution in the key step2010In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 13, p. 4596-4599Article in journal (Refereed)
    Abstract [en]

    An enantioselective synthesis of (R)-bufuralol via a ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) has been achieved. The synthesis starts from readily available 2-ethylphenol and provides (R)-bufuralol in high ee and a good overall yield of 31%.

  • 37.
    Johnston, Eric V.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oxidation of carbonyl compounds2010In: Modern Oxidation Methods / [ed] Jan-Erling Bäckvall, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 2, p. 353-369Chapter in book (Other academic)
  • 38.
    Johnston, Eric V
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Karlsson, Erik A
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lee, Bao-Lin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Novel dinuclear Ru-complex for water oxidation2010In: Abstracts of Papers, 240th ACS National Meeting, Boston, MA, United States, August 22-26, 2010 (2010), American Chemical Society , 2010Conference paper (Other academic)
  • 39.
    Johnston, Eric V.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Karlsson, Erik A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tran, Lien-Hoa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient aerobic ruthenium-catalyzed oxidation of secondary alcohols by the use of a hybrid electron transfer catalyst2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 10, p. 1971-1976Article in journal (Refereed)
    Abstract [en]

    Biomimetic aerobic oxidation of secondary alcohols has been performed using hybrid catalyst 1 and Shvo's catalyst 2. This combination allows mild reaction conditions and low catalytic loading, due to the efficiency of intramolecular electron transfer. By this method a wide range of different alcohols have been converted into their corresponding ketones. Oxidation of benzylic as well as aliphatic, electron-rich, electron-deficient and sterically hindered alcohols could be oxidized in excellent yield and selectivity. Oxidation of (S)-1-phenyl-ethanol showed that no racemization occurred during the course of the reaction, indicating that the hydride 2b adds to the quinone much faster than it re-adds to the ketone product. The kinetic deuterium isotope effect of the oxidation was determined by the use of 1-phenylethanol (3a) and 1-deuterio-1-phenylethanol (3a-d1) in parallel and competitive manner, which gave the same isotope effect within experimental error (k(H)/k(D) approximate to 2.8). This indicates that there is no strong coordination of the substrate to the catalyst.

  • 40.
    Jonsson, Hanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Exploring the structure of oligo- and polysaccharides: Synthesis and NMR spectroscopy studies2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    A deeper understanding of the diversity of carbohydrates and the many applications of oligo- and polysaccharides found in nature are of high interest. Many of the processes involving carbohydrates affect our everyday life. This thesis is based on six papers all contributing to an extended perspective of carbohydrate property and functionality. An introduction to carbohydrate chemistry together with a presentation of selected carbohydrate synthesis and analysis methods introduces the reader to the research field. The first paper is an NMR spectroscopy reinvestigation of the structures of the O-antigens from the lipopolysaccharides (LPS) of Shigella dysenteriae type 3 and Escherichia coli O124. The repeating units were concluded to be built of identical branched pentasaccharides now with the correct anomeric configurations. Paper II is a structural investigation of the O-antigen from the LPS of E. coli O74 which is built of branched tetrasaccharide repeating units including the uncommon monosaccharide d-Fuc3NAc. Paper III is a conformational study of a rhamnose derivative, using NMR spectroscopy and X-ray crystallography. The benzoyl ester group positioned at C4 prefers an “eclipsed” conformation in the crystal as well as in solution. The use of site-specifically 13C-labeled compounds in conformational studies is discussed in Papers IV and V. The disaccharide α-L-Rhap-(1→2)-α-L-Rhap-OMe was synthesized together with two 13C-isotopologues and studied with NMR spectroscopy to give seven J-couplings related to torsion angles φ and ψ. The trisaccharide α-L-Rhap-(1→2)[α-L-Rhap-(1→3)]-α-L-Rhap-OMe was synthesized with 13C-labeling at two positions which presented a solution to a problem of overlapping signals in the 1H NMR spectrum. The site-specific labeling also facilitated the measurement of two 3JCC and two 2JCH coupling constants. Finally, chapter 6 gives a short introduction to glycosynthase chemistry and discusses the synthesis of α-glycosyl fluorides. A novel cyclic heptasaccharide was synthesized from α-laminariheptaosyl fluoride using a mutant of the enzyme laminarase 16A and subsequently analyzed by NMR spectroscopy.

  • 41.
    Kalek, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jezowska, Martina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-catalyzed propargylic substitution with phosphorus nucleophiles2010In: Abstracts of Papers, 240th ACS National Meeting, Boston, MA, United States, August 22-26, 2010, Washington, D C: American Chemical Society , 2010Conference paper (Other academic)
  • 42.
    Kalek, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johansson, Tommy
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jezowska, Martina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-catalyzed propargylic substitution with phosphorus nucleophiles: efficient, stereoselective synthesis of allenylphosphonates and related compounds2010In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 12, no 20, p. 4702-4704Article in journal (Refereed)
    Abstract [en]

    A new, efficient method is developed, based on a palladium(0)-catalyzed reaction of propargylic derivatives with various phosphorus nucleophiles, to produce allenylphosphonates and their analogues with defined stereochemistry in the allenic and the phosphonate moiety. 

  • 43.
    Krumlinde, Patrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric synthesis of bicyclic diol derivatives through metal and enzyme catalysis: Application to the formal synthesis of sertraline2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 13, p. 4031-4036Article in journal (Refereed)
    Abstract [en]

    Enzyme- and ruthenium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of bicyclic diols to their diacetates was highly enantio- and diastereoselective to give the corresponding diacetates in high yield with high enantioselectivity (99.9 % ee). The enantiomerically pure diols are accessible by simple hydrolysis (NaOH, MeOH), but an alternative enzyme-catalyzed ester cleavage was also used to give the trans-diol (R,R)-1 b in extremely high diastereomeric purity (trans/cis=99.9:0.1, >99.9 % ee). It was demonstrated that the diols can be selectively oxidized to the ketoalcohols in a ruthenium-catalyzed Oppenauer-type reaction. A formal enantioselective synthesis of sertraline from a simple racemic cis/trans diol 1 b was demonstrated.

  • 44.
    Kärkäs, Markus
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bio-inspired metal complexes: Their synthesis and application in light-driven water oxidation and organic transformations2010Licentiate thesis, comprehensive summary (Other academic)
  • 45.
    Laakso, Johanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borbas, Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Towards lanthanide-based responsive luminescent probes for the detection of reactive oxygen species2010In: Abstracts of Papers, 240th ACS National Meeting, Boston, MA, United States, August 22-26, 2010, American Chemical Society , 2010Conference paper (Other academic)
  • 46.
    Landström, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Glycan flexibility: insights into nanosecond dynamics from a microsecond molecular dynamics simulation explaining an unusual nuclear Overhauser effect2010In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 345, no 2, p. 330-333Article in journal (Refereed)
  • 47.
    Larsson, Johanna M
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aydin, Juhanes
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic functionalization of allylic compounds via palladium(IV) intermediates2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, American Chemical Society , 2010Conference paper (Other academic)
  • 48.
    Lavén, Gaston
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis focuses on chemical transformations of H-phosphonate and H-phosphonothioate and can be divided in two parts. The first part, is devoted to the development of the palladium-catalyzed P-C bond formation. Both mechanistic and synthetic studies of the transformations have been performed. The stereochemical aspects of palladium catalyzed arylation and benzylation of DNA analogs containing H-phosphonate and H-phosphonothioate have been studied.

    In chapter 5 the condensation using Mitsunobu reaction of H-phosphonate function and nucleoside has been studied. Efficient protocols for the synthesis of nucleoside H-phosphonate monoester were developed.

    The last chapter deals with development of silylation-mediated transesterfication of phenyl H-phosphonothioate as a thiophosphonylating agent. The methodology was used to prepare nucleoside H-phosphonothioate monomeric building blocks in good yields.

  • 49.
    Lavén, Gaston
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kalek, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jezowska, Martina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonate diesters with benzyl halides. Synthetic and mechanistic studies2010In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 34, no 5, p. 967-975Article in journal (Refereed)
    Abstract [en]

    We have developed a new, efficient method for the synthesis of benzylphosphonate andbenzylphosphonothioate diesters via a palladium(0)-catalyzed cross-coupling reaction betweenbenzyl halides and H-phosphonate or H-phosphonothioate diesters, using Pd2(dba)3(CHCl3)as a palladium source and Xantphos as a supporting ligand. Some mechanistic aspects of thesereactions were investigated using 31P NMR spectroscopy.

  • 50.
    Lee, Bao-Lin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Inge, Andrew K.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Tran, Lien-Hoa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Xu, Yunhua
    Hansson, Örjan
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis and characterization of oligonuclear Ru, Co, and Cu oxidation catalysts2010In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 34, p. 5462-5470Article in journal (Refereed)
    Abstract [en]

    In this work, we report the preparation and crystal structures of three new oligonuclear complexes, Ru-2(bbpmp)(mu-OAc)(3) (4), [Co-2(bbpmp)(mu-OAc)(mu-OMe)](PF6) (5), [Cu-4(Hbbpmp)(2)(mu-OAc)(H2O)(2)](OAc)(PF6)(2) (6) {H(3)bbpmp = 2,6-bis[(2-hydroxybenzyl)-(2-pyridylmethyl)aminomethyl]-4-methylphenol (3)}. The structures of the complexes were determined by single-crystal X-ray diffraction. The oxidation states of ruthenium, cobalt and copper in the complexes are +3, +3 and +2, respectively. In 4 and 5, Ru-III and Co-III are coordinated to four oxygen and two nitrogen atoms in an octahedral geometry, while in 6, Cu-II adopts both octahedral (CuN2O4) and square-pyramidal (CuN2O3) geometry. The potential of the three complexes as oxidation catalysts has been investigated.

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