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  • 1. Abrahamsson, Maria
    et al.
    Lundqvist, Maria J.
    Wolpher, Henriette
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johansson, Olof
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Bergquist, Jonas
    Rasmussen, Torben
    Becker, Hans-Christian
    Hammarström, Leif
    Norrby, Per-Ola
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Petter
    Steric influence on the excited-state lifetimes of ruthenium complexes with bipyridyl-alkanylene-pyridyl ligands2008In: Inorganic Chemistry, ISSN 0020-1669, Vol. 47, no 9, p. 3540-3548Article in journal (Refereed)
  • 2.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Alkene and Imino Reductions by Organocatalysis2008In: Modern Reduction Methods, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, p. 341-361Chapter in book (Refereed)
  • 3.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Product Class 2: Epoxides (Oxiranes): Synthesis from Alkenes by Metal-Mediated Oxidation2008In: Houben-Weyl Methods of Molecular Transformations: Compounds with One Saturated Carbon-Heteroatom Bond, Georg Thieme Verlag KG, Stuttgart , 2008, p. 227-276Chapter in book (Refereed)
  • 4.
    Ahlford, Katrin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalyzed asymmetric transfer hydrogenation of ketones. Ligand development and mechanistic investigation2008Licentiate thesis, comprehensive summary (Other academic)
  • 5.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lind, Jesper
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Mäler, Lena
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalyzed asymmetric transfer hydrogenation of alkyl and aryl ketones in aqueous media2008In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 10, no 8, p. 832-835Article in journal (Refereed)
    Abstract [en]

    A novel lipophilic rhodium catalyst was evaluated in the enantioselective transfer hydrogenation of ketones in water using sodium formate as the hydride donor, and in the presence of sodium docecylsulfonate. Alkyl alkyl ketones were reduced in good yields and in moderate to good enantioselectivities, and the reduction of aryl alkyl ketones proceeded with excellent enantioselectivity (up to 97% ee).

  • 6.
    Akhtar, Tashfeen
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Unusual synthesis of carbohydrate sec-sec ether-linked pseudodisaccharides2008In: Carbohydrate Research, ISSN 0008-6215, Vol. 343, no 12, p. 2094-2100Article in journal (Refereed)
  • 7. Alexakis, A.
    et al.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Krause, N.
    Pàmies, O.
    Diéguez, M.
    Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions2008In: Chemical Reviews, ISSN 0009-2665, Vol. 108, no 8, p. 2796-2823Article in journal (Refereed)
  • 8.
    Ali, Tara
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Weintraub, Andrej
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Structural studies of the O-antigenic polysaccharides from the enteroaggregative Escherichia coli strain 87/D2 and international type strains from E. coli O1282008In: Carbohydrate Research, ISSN 0008-6215, Vol. 343, no 4, p. 695-702Article in journal (Refereed)
  • 9.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Conrad, Cathrin S.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stereoselective pincer-complex catalyzed C-H functionalization of benzyl nitriles under mild conditions. An efficient route to β-aminonitriles2008In: Organic Letters, ISSN 1523-7060, Vol. 10, no 22, p. 5175-5178Article in journal (Refereed)
  • 10.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rydén, Andreas
    Szabó, Kálmán J.
    Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate2008In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 19, no 15, p. 1867-1870Article in journal (Refereed)
  • 11.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Senthil Kumar, Kuppusamy
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanistic studies of the palladium pincer complex-catalyzed condensation of sulfonimines and isocyanoacetate to imidazoline derivatives2008In: Abstracts of Papers, 235th ACS National Meeting, New Orleans, LA, United States, April 6-10, 2008, 2008Conference paper (Other academic)
  • 12.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective palladium pincer complex catalyzed carbon carbon coupling reactions between tosylimines and various nucleophiles2008In: Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, Washington, DC: American Chemical Society , 2008Conference paper (Other academic)
  • 13.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-pincer complex catalyzed C-C coupling of allyl nitriles with tosyl imines via regioselective allylic C-H bond functionalization2008In: Organic Letters, ISSN 1523-7060, Vol. 10, no 13, p. 2881-2884Article in journal (Refereed)
    Abstract [en]

    A mechanistically new palladium-pincer complex catalyzed allylation of sulfonimines is presented. This reaction involves C-H bond functionalization of allyl nitriles under mild conditions. The reaction proceeds with a high regioselectivity, without allyl rearrangement of the product. Modeling studies indicate that the carbon-carbon bond formation process proceeds via (η1-allyl)palladium pincer complex intermediates.

  • 14.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanistic considerations for the enantioselective palladium pincer complex catalyzed carbon-carbon coupling reactions2008In: Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, Washington, DC: American Chemical Society , 2008Conference paper (Other academic)
  • 15.
    Ayesa Alvarez, Susana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Design and Synthesis of Amine Building Blocks and Protease Inhibitors2008Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first part of this thesis addresses the design and synthesis of amine building blocks accomplished by applying two different synthetic procedures, both of which were developed using solid-phase chemistry. Chapter 1 presents the first of these methods, entailing a practical solid-phase parallel synthesis route to N-monoalkylated aminopiperidines and aminopyrrolidines achieved by selective reductive alkylation of primary and/or secondary amines. Solid-phase NMR spectroscopy was used to monitor the reactions for which a new pulse sequence was developed. The second method, reported in Chapter 2, involves a novel approach to the synthesis of secondary amines starting from reactive alkyl halides and azides. The convenient solid-phase protocol that was devised made use of the Staudinger reaction in order to accomplish highly efficient alkylations of N-alkyl phosphimines or N-aryl phosphimines with reactive alkyl halides.

    The second part of the thesis describes the design and synthesis of three classes of protease inhibitors targeting the cysteine proteases cathepsins S and K, and the serine protease hepatitis C virus (HCV) NS3 protease. Chapter 4 covers the design, solid-phase synthesis, and structure-activity relationships of 4-amidofurane-3-one P1-containing inhibitors of cathepsin S and the effects of P3 sulfonamide groups on the potency and selectivity towards related cathepsin proteases. This work resulted in the discovery of highly potent and selective inhibitors of cathepsin S. Two parallel solid-phase approaches to the synthesis of a series of aminoethylamide inhibitors of cathepsin K are presented in Chapter 5. Finally, Chapter 6 reports peptide-based HCV NS3 protease inhibitors containing a non-electrophilic allylic alcohol moiety as P1 group and also outlines efforts to incorporate this new template into low-molecular-weight drug-like molecules.

  • 16.
    Ayesa, Susana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samuelsson, Bertil
    Classon, Björn
    A One-Pot, Solid-Phase Synthesis of Secondary Amines from Reactive Alkyl Halides and an Alkyl Azide2008In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 1, p. 77-79Article in journal (Refereed)
  • 17. Back, Marcus
    et al.
    Nyhlen, Jonas
    Kvarnstrom, Ingemar
    Appelgren, Sara
    Borkakoti, Neera
    Jansson, Katarina
    Lindberg, Jimmy
    Nystrom, Susanne
    Hallberg, Anders
    Rosenquist, Asa
    Samuelsson, Bertil
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Design, synthesis and SAR of potent statine-based BACE-1 inhibitors: Exploration of P1 phenoxy and benzyloxy residues2008In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 16, no 21, p. 9471-9486Article in journal (Refereed)
    Abstract [en]

    Several BACE-1 inhibitors with low nanomolar level activities, encompassing a statine-based core structure with phenyloxymethyl- and benzyloxymethyl residues in the P1 position, are presented. The novel P1 modi. cation introduced to allow the facile exploration of the S1 binding pocket of BACE-1, delivered highly promising inhibitors.

  • 18.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kalek, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies2008In: Tetrahedron, ISSN 0040-4020, Vol. 64, no 37, p. 8843-8850Article in journal (Refereed)
  • 19.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kalek, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of nucleoside phosphorothio-, phosphorodithio- and phophoroselenoate diesters via oxidative esterification of the corresponding H-phosphonate analogues2008In: Collection Symposium Series, Vol. 10, 2008, p. 219-223Conference paper (Other academic)
  • 20.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kalek, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The case for the intermediacy of monomeric metaphosphate analogues during oxidation of H-phosphonothioate, H-phosphonodithioate, and H-phosphonoselenoate monoesters: mechanistic and synthetic studies2008In: The Journal of Organic Chemistry, ISSN 0022-3263, Vol. 73, no 13, p. 5029-5038Article in journal (Refereed)
  • 21.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient synthesis of beta-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates2008In: Chemistry: a European Journal, ISSN 0947-6539, Vol. 14, no 34, p. 10547-10550Article in journal (Refereed)
  • 22.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of b-Hydroxy Ketones from Allylic Alcohols via Catalytic Formation of Ruthenium Enolates2008In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 34, p. 10547-10550Article in journal (Refereed)
    Abstract [en]

    The most efficient Ru-catalyzed isomerization–aldol reaction from allylic alcohols has been achieved by using [η5-(Ph5Cp)Ru(CO)2Cl] as the catalyst. The bulky pentaphenylcyclopentadienyl ligand on the ruthenium atom prevents protonation at the oxygen of the Ru–enolate intermediate and completely suppresses the formation of unwanted ketone byproducts (see scheme). The domino transformation is as good as it can be: aldols are obtained in quantitative yields at ambient temperature.

  • 23.
    Bielawski, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient and High-Yielding Routes to Diaryliodonium Salts2008Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis summarizes three novel and general reaction protocols for the synthesis of diaryliodonium salts. All protocols utilize mCPBA as oxidant and the acids used are either TfOH, to obtain triflate salts, or BF3•Et2O that gives the corresponding tetrafluoroborate salts in situ.

    Chapter two describes the reaction of various arenes and aryl iodides, delivering electron-rich and electron-deficient triflates in moderate to excellent yields.

    In chapter three, it is shown that the need of aryl iodides can be circumvented, as molecular iodine can be used together with arenes in a direct one-pot, three-step synthesis of symmetric diaryliodonium triflates.

    The final and fourth chapter describes the development of a sequential one-pot reaction from aryl iodides and boronic acids, delivering symmetric and unsymmetric, electron-rich and electron-deficient iodonium tetrafluoroborates in moderate to excellent yields. This protocol was developed to overcome mechanistic limitations existing in the protocols described in chapter two and three.

    The methodology described in this thesis is the most general, efficient and high-yielding existing up to date, making diaryliodonium salts easily available for various applications in synthesis.

  • 24.
    Bielawski, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aili, David
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides2008In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, no 12, p. 4602-4607Article in journal (Refereed)
    Abstract [en]

    Diaryliodonium salts have recently received considerable attention as mild arylation reagents in organic synthesis. This paper describes a regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations. The protocol is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.

  • 25.
    Borén, Linnéa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective Synthesis of Sec-Alcohol Derivatives and Diols via Combined Ruthenium and Enzyme Catalysis2008Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first part of this thesis describes the synthesis of enantiopure secondary alcohol derivatives. These syntheses are carried out via the combination of an enzyme as a resolution catalyst and a ruthenium catalyst as a racemization catalyst, in what is called dynamic kinetic resolution (DKR). By varying the resolution catalyst enantio-complementary processes can be obtained. A lipase (PS-C II) catalyzed DKR of γ-hydroxyamides gave the corresponding (R)-acetates in high yields and with high enantioselectivity. The synthetic usefulness of these obtained (R)-acetates was demonstrated by the synthesis of (R)-5-methyltetrahydrofurane-2-one. A protease (Subtilisin Carlsberg) catalyzed DKR of various secondary alcohols gave the corresponding (S)-acetates in high yields and with high enantioselectivity. In the second part of this thesis the DKR process has been extended into a dynamic kinetic asymmetric transformation (DYKAT) of diols. Various 1,5- and 1,4-diols were transformed into enantiopure diacetates in a lipase (CALB and PS-C II) catalyzed DYKAT. The synthetic utility of the obtained enantiopure diacetates were demonstrated by the synthesis of various enantiopure disubstituted heterocycles.

  • 26.
    Covarrubias, Adrian Suarez
    et al.
    Department of Cell and Molecular Biology, Uppsala University, Sweden.
    Högbom, Martin
    Department of Cell and Molecular Biology, Uppsala University, Sweden.
    Bergfors, Terese
    Department of Cell and Molecular Biology, Uppsala University, Sweden.
    Carroll, Paul
    Institute for Cell and Molecular Science, Barts and the London School of Medicine and Dentistry, London.
    Mannerstedt, Karin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Parish, Tanya
    Institute for Cell and Molecular Science, Barts and the London School of Medicine and Dentistry, London.
    Jones, T Alwyn
    Department of Cell and Molecular Biology, Uppsala University, Sweden.
    Mowbray, Sherry L
    Department of Molecular Biology, Swedish University of Agricultural Sciences, Biomedical Center, Uppsala, Sweden.
    Structural, biochemical, and in vivo investigations of the threonine synthase from Mycobacterium tuberculosis.2008In: Journal of Molecular Biology, ISSN 0022-2836, E-ISSN 1089-8638, Vol. 381, no 3, p. 622-33Article in journal (Refereed)
    Abstract [en]

    Threonine biosynthesis is a general feature of prokaryotes, eukaryotic microorganisms, and higher plants. Since mammals lack the appropriate synthetic machinery, instead obtaining the amino acid through their diet, the pathway is a potential focus for the development of novel antibiotics, antifungal agents, and herbicides. Threonine synthase (TS), a pyridoxal-5-phosphate-dependent enzyme, catalyzes the final step in the pathway, in which L-homoserine phosphate and water are converted into threonine and inorganic phosphate. In the present publication, we report structural and functional studies of Mycobacterium tuberculosis TS, the product of the rv1295 (thrC) gene. The structure gives new insights into the catalytic mechanism of TSs in general, specifically by suggesting the direct involvement of the phosphate moiety of the cofactor, rather than the inorganic phosphate product, in transferring a proton from C4' to C(gamma) in the formation of the alphabeta-unsaturated aldimine. It further provides a basis for understanding why this enzyme has a higher pH optimum than has been reported elsewhere for TSs and gives rise to the prediction that the equivalent enzyme from Thermus thermophilus will exhibit similar behavior. A deletion of the relevant gene generated a strain of M. tuberculosis that requires threonine for growth; such auxotrophic strains are frequently attenuated in vivo, indicating that TS is a potential drug target in this organism.

  • 27.
    Cribiù, Riccardo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides2008In: Chemical Communications, ISSN 1359-7345, no 10, p. 1246-1248Article in journal (Refereed)
  • 28.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Intramolecular aglycon delivery2008In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 343, no 10-11, p. 1553-1573Article, review/survey (Other academic)
  • 29.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gehrke, Sebastian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Erfan, Sayeh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cribiù, Riccardo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Studies on the synthesis of valienamine and 1-epi-valienamine starting from D-glucose or L-sorbose2008In: Carbohydrate Research, ISSN 0008-6215, Vol. 343, no 10-11, p. 1675-1692Article in journal (Refereed)
  • 30.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric amino acid catalysis2008In: Recent Devlopments in Physical Chemistry, 3rd Mexican Meeting on Mathematical and Experimental Physics, 2008, p. 47-59Conference paper (Refereed)
  • 31.
    Córdova, Armando
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Direct Catalytic Asymmetric Mannich Reactions and Surroundings2008In: Amino Group Chemistry. From Synthesis to the Life Sciences., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, p. 185-205Chapter in book (Refereed)
  • 32. Dutheuil, Guillaume
    et al.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aggarwal, Varinder K.
    Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts2008In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 14, p. 2293-2297Article in journal (Refereed)
    Abstract [en]

    A remarkably simple and effective system for the direct conversion of allylic alcohols into high value allylic boronic esters using commercially available reagents and catalysts is described.

  • 33.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric Organocatalytic Aldol and Mannich Reactions Catalyzed by Amino Acid-Derivatives and Small Peptides with a Primary Amine Functionality2008Licentiate thesis, comprehensive summary (Other academic)
  • 34.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives2008In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, no 5, p. 803-807Article in journal (Refereed)
    Abstract [en]

    Highly enantioselective, amino acid-catalyzed, one-pot three-component asymmetric Mannich reactions between dihydroxyacetone, p-anisidine, and aldehydes are presented. The reactions proceeded with high chemo- and stereoselectivity and furnished the corresponding α,α′-dihydroxy-β-aminoketones in high yields with 82–95% ee.

  • 35.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready alpha-hydroxy-beta-amino acids2008In: Tetrahedron Letters, ISSN 0040-4039, Vol. 49, no 47, p. 6631-6634Article in journal (Refereed)
    Abstract [en]

    A highly enantioselective catalytic route to protected β-amino-α-hydroxy acids, such as the side chain of Taxotere, is presented. The organocatalytic asymmetric reactions between unmodified protected α-oxyaldehydes and N-Boc-protected aryl imines give the corresponding compound with up to >19:1 dr and 99–99% ee.

  • 36.
    Ericsson, Daniel J.
    et al.
    1Department of Cell and Molecular Biology, Uppsala University, Biomedical Center.
    Kasrayan, Alex
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johansson, Patrik
    1Department of Cell and Molecular Biology, Uppsala University, Biomedical Center.
    Bergfors, Terese
    1Department of Cell and Molecular Biology, Uppsala University, Biomedical Center.
    Sandström, Anders G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mowbray, Sherry L.
    Department of Molecular Biology, Swedish University of Agricultural Sciences, Biomedical Center.
    X-Ray structure of Candida antarctica lipase A shows a novel lid structure and a likely mode of interfacial activation2008In: Journal of Molecular Biology, ISSN 0022-2836, Vol. 376, no 1, p. 109-119Article in journal (Refereed)
    Abstract [en]

    In nature, lipases (EC 3.1.1.3) catalyze the hydrolysis of triglycerides to form glycerol and fatty acids. Under the appropriate conditions, the reaction is reversible, and so biotechnological applications commonly make use of their capacity for esterification as well as for hydrolysis of a wide variety of compounds. In the present paper, we report the X-ray structure of lipase A from Candida antarctica, solved by single isomorphous replacement with anomalous scattering, and refined to 2.2-Å resolution. The structure is the first from a novel family of lipases. Contrary to previous predictions, the fold includes a well-defined lid as well as a classic α/β hydrolase domain. The catalytic triad is identified as Ser184, Asp334 and His366, which follow the sequential order considered to be characteristic of lipases; the serine lies within a typical nucleophilic elbow. Computer docking studies, as well as comparisons to related structures, place the carboxylate group of a fatty acid product near the serine nucleophile, with the long lipid tail closely following the path through the lid that is marked by a fortuitously bound molecule of polyethylene glycol. For an ester substrate to bind in an equivalent fashion, loop movements near Phe431 will be required, suggesting the primary focus of the conformational changes required for interfacial activation. Such movements will provide virtually unlimited access to solvent for the alcohol moiety of an ester substrate. The structure thus provides a basis for understanding the enzyme's preference for acyl moieties with long, straight tails, and for its highly promiscuous acceptance of widely different alcohol and amine moieties. An unconventional oxyanion hole is observed in the present structure, although the situation may change during interfacial activation

  • 37.
    Eriksson, Lars
    et al.
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Widmalm, Göran
    Department of Organic Chemistry.
    Methyl 3-O-alpha-D-mannopyranosyl beta-D-glucopyranoside tetrahydrate2008In: Acta Crystallographica Section E, ISSN 1600-5368, Vol. E64, no 8, p. o1639-o1640Article in journal (Refereed)
  • 38.
    Frigell, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Towards Carbasugar-Based Mimics of Mycobacerial Arabinogalactan2008Licentiate thesis, comprehensive summary (Other academic)
  • 39.
    Färnbäck, Magnus
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Methyl 2-O-beta-L-fucopyranosyl alpha-D-glucopyranoside monohydrate: a synchrotron study2008In: Acta Crystallographica Section C, ISSN 0108-2701, Vol. 64, no 2, p. o31-o32Article in journal (Refereed)
  • 40. Gagliardo, Marcella
    et al.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mehendale, Nilesh C.
    van Koten, Gerard
    Klein Gebbink, Robertus J. M.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes: synthesis and tandem catalytic activity of the first PCS-pincer palladium complex2008In: Chemistry: a European journal, ISSN 0947-6539, Vol. 14, no 16, p. 4800-4809Article in journal (Refereed)
  • 41. Gao, Weiming
    et al.
    Liu, Jianhui
    Jiang, Weina
    Wang, Mei
    Weng, Linhong
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    An azadithiolate bridged Fe2S2 complex as active site model of FeFe-hydrogenase covalently linked to a Re(CO)3(bpy)(py) photosensitizer aiming for light-driven hydrogen production2008In: Comptes Rendus Chimie, ISSN 1631-0748, Vol. 11, no 8, p. 915-921Article in journal (Refereed)
  • 42. González, David
    et al.
    Grilló, María-Jesús
    De Miguel, María-Jesús
    Ali, Tara
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Arce-Gorvel, Vilma
    Delrue, Rose-May
    Conde-Álvarez, Raquel
    Munoz, Pilar
    López-Goni, Ignacio
    Iriarte, Maite
    Marín, Clara-M.
    Weintraub, Andrej
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zygmunt, Michel
    Letesson, Jean-Jacques
    Gorvel, Jean-Pierre
    Blasco, José-María
    Moriyón, Ignacio
    Brucellosis vaccines: assessment of Brucella melitensis lipopolysaccharide rough mutants defective in core and O-polysaccharide synthesis and export2008In: PLoS ONE, ISSN 1932-6203, Vol. 3, no 7, p. e2760 (1-15)Article in journal (Refereed)
  • 43. Gupta, Garima
    et al.
    Gemma, Emiliano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Surolia, Avadhesha
    Defining substrate interactions with calreticulin: an isothermal titration calorimetric study2008In: Glycoconjugate Journal, ISSN 0282-0080, Vol. 25, no 8, p. 797-802Article in journal (Refereed)
  • 44. Hammar, Peter
    et al.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Density functional theory study of the stereoselectivity in small peptide-catalyzed intermolecular aldol reactions2008In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 19, no 13, p. 1617-1621Article in journal (Refereed)
  • 45.
    Hoben, Christine E.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kanupp, Lisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Practical chemoenzymatic dynamic kinetic resolution of primary amines via transfer of a readily removable benzyloxycarbonyl group2008In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, no 6, p. 977-979Article in journal (Refereed)
  • 46.
    Híresová, Renáta
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Studies on Nucleotide Analogues Containing P-S-C Bond2008Licentiate thesis, comprehensive summary (Other academic)
  • 47.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hammar, Peter
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Organocatalytic asymmetric hydrophosphination of alpha,beta-unsaturated aldehydes: Development, mechanism and DFT calculations2008In: Advanced Synthesis & Catalysis, ISSN 1615-4150, Vol. 350, no 11-12, p. 1875-1884Article in journal (Refereed)
  • 48.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramon
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to beta-amino acids2008In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 7, p. 1153-1157Article in journal (Refereed)
    Abstract [en]

    The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and a,p-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or gamma-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding beta-amino acids is also described.

  • 49.
    Ibrahem, Ismail
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    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.
    Sundén, Henrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    One-pot organocatalytic domino Michael/alpha-alkylation reactions: direct catalytic enantioselective cyclopropanation and cyclopentanation reactions2008In: Chemistry: a European journal, ISSN 0947-6539, Vol. 14, no 26, p. 7867-7879Article in journal (Refereed)
  • 50.
    Johansson, Mikael
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Development of Biomimetic Catalytic Systems for Selective Oxidations with H2O2 and O22008Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Four different catalytic systems were studied for biomimetic coupled oxidations using H2O2 or O2. In the first example, osmium tetroxide works as a substrate-selective catalyst for dihydroxylation of olefins. Electron transfer to H2O2 is facilitated by electron transfer mediators (ETMs). In one case VO(acac)2 or MeReO3 was used as ETM; in the other case a combination of flavin and tertiary amine was used as ETMs. These three systems were immobilized in the ionic liquid [bmim]PF6 for the purpose of recycling of the catalyst.

    In the second example, an organocatalyst (a flavin) was used for the oxidation of sulfides to sulfoxides and this catalytic system was recycled and reused in an ionic liquid.

    In the third example, primary aromatic amines were oxidized by H2O2 to nitroso compounds in a selenium-catalyzed oxidation. The nitrosoarenes were used in a one-pot hetero Diels-Alder reaction with dienes forming 1,2-oxazines.

    In the fourth example, a cobalt salophen complex was immobilized in different zeolites. The catalyst was used in aerobic oxidation of p-hydroquinone and the zeolite catalyst could be reused. The oxidative carbocyclization of ene-allenes was tested successfully using the triple catalytic system consisting of palladium(II), p-benzoquinone, and the immobilized catalyst for O2 activation.

    All these systems gave mild and selective oxidations with environmentally friendly and inexpensive terminal oxidants.

123 1 - 50 of 124
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