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  • 1. Abrahamsson, Maria
    et al.
    Lundqvist, Maria J.
    Wolpher, Henriette
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johansson, Olof
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Eriksson, Lars
    Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Bergquist, Jonas
    Rasmussen, Torben
    Becker, Hans-Christian
    Hammarström, Leif
    Norrby, Per-Ola
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Persson, Petter
    Steric influence on the excited-state lifetimes of ruthenium complexes with bipyridyl-alkanylene-pyridyl ligands2008Inngår i: Inorganic Chemistry, ISSN 0020-1669, Vol. 47, nr 9, s. 3540-3548Artikkel i tidsskrift (Fagfellevurdert)
  • 2.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Alkene and Imino Reductions by Organocatalysis2008Inngår i: Modern Reduction Methods, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, s. 341-361Kapittel i bok, del av antologi (Fagfellevurdert)
  • 3.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Product Class 2: Epoxides (Oxiranes): Synthesis from Alkenes by Metal-Mediated Oxidation2008Inngår i: Houben-Weyl Methods of Molecular Transformations: Compounds with One Saturated Carbon-Heteroatom Bond, Georg Thieme Verlag KG, Stuttgart , 2008, s. 227-276Kapittel i bok, del av antologi (Fagfellevurdert)
  • 4.
    Ahlford, Katrin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rhodium-catalyzed asymmetric transfer hydrogenation of ketones. Ligand development and mechanistic investigation2008Licentiatavhandling, med artikler (Annet vitenskapelig)
  • 5.
    Ahlford, Katrin
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lind, Jesper
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för biokemi och biofysik.
    Mäler, Lena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för biokemi och biofysik.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rhodium-catalyzed asymmetric transfer hydrogenation of alkyl and aryl ketones in aqueous media2008Inngår i: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 10, nr 8, s. 832-835Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Eriksson, Lars
    Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Cumpstey, Ian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Unusual synthesis of carbohydrate sec-sec ether-linked pseudodisaccharides2008Inngår i: Carbohydrate Research, ISSN 0008-6215, Vol. 343, nr 12, s. 2094-2100Artikkel i tidsskrift (Fagfellevurdert)
  • 7. Alexakis, A.
    et al.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Krause, N.
    Pàmies, O.
    Diéguez, M.
    Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions2008Inngår i: Chemical Reviews, ISSN 0009-2665, Vol. 108, nr 8, s. 2796-2823Artikkel i tidsskrift (Fagfellevurdert)
  • 8.
    Ali, Tara
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Weintraub, Andrej
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Structural studies of the O-antigenic polysaccharides from the enteroaggregative Escherichia coli strain 87/D2 and international type strains from E. coli O1282008Inngår i: Carbohydrate Research, ISSN 0008-6215, Vol. 343, nr 4, s. 695-702Artikkel i tidsskrift (Fagfellevurdert)
  • 9.
    Aydin, Juhanes
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Conrad, Cathrin S.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Szabó, Kálmán J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stereoselective pincer-complex catalyzed C-H functionalization of benzyl nitriles under mild conditions. An efficient route to β-aminonitriles2008Inngår i: Organic Letters, ISSN 1523-7060, Vol. 10, nr 22, s. 5175-5178Artikkel i tidsskrift (Fagfellevurdert)
  • 10.
    Aydin, Juhanes
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rydén, Andreas
    Szabó, Kálmán J.
    Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate2008Inngår i: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 19, nr 15, s. 1867-1870Artikkel i tidsskrift (Fagfellevurdert)
  • 11.
    Aydin, Juhanes
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Senthil Kumar, Kuppusamy
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Szabó, Kálmán J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mechanistic studies of the palladium pincer complex-catalyzed condensation of sulfonimines and isocyanoacetate to imidazoline derivatives2008Inngår i: Abstracts of Papers, 235th ACS National Meeting, New Orleans, LA, United States, April 6-10, 2008, 2008Konferansepaper (Annet vitenskapelig)
  • 12.
    Aydin, Juhanes
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Szabó, Kálmán
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Enantioselective palladium pincer complex catalyzed carbon carbon coupling reactions between tosylimines and various nucleophiles2008Inngår i: Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, Washington, DC: American Chemical Society , 2008Konferansepaper (Annet vitenskapelig)
  • 13.
    Aydin, Juhanes
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Szabó, Kálmán
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Palladium-pincer complex catalyzed C-C coupling of allyl nitriles with tosyl imines via regioselective allylic C-H bond functionalization2008Inngår i: Organic Letters, ISSN 1523-7060, Vol. 10, nr 13, s. 2881-2884Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Szabó, Kálmán J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mechanistic considerations for the enantioselective palladium pincer complex catalyzed carbon-carbon coupling reactions2008Inngår i: Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, Washington, DC: American Chemical Society , 2008Konferansepaper (Annet vitenskapelig)
  • 15.
    Ayesa Alvarez, Susana
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Design and Synthesis of Amine Building Blocks and Protease Inhibitors2008Doktoravhandling, med artikler (Annet vitenskapelig)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Samuelsson, Bertil
    Classon, Björn
    A One-Pot, Solid-Phase Synthesis of Secondary Amines from Reactive Alkyl Halides and an Alkyl Azide2008Inngår i: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, nr 1, s. 77-79Artikkel i tidsskrift (Fagfellevurdert)
  • 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
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Design, synthesis and SAR of potent statine-based BACE-1 inhibitors: Exploration of P1 phenoxy and benzyloxy residues2008Inngår i: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 16, nr 21, s. 9471-9486Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kalek, Marcin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stawinski, Jacek
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies2008Inngår i: Tetrahedron, ISSN 0040-4020, Vol. 64, nr 37, s. 8843-8850Artikkel i tidsskrift (Fagfellevurdert)
  • 19.
    Bartoszewicz, Agnieszka
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kalek, Marcin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stawinski, Jacek
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis of nucleoside phosphorothio-, phosphorodithio- and phophoroselenoate diesters via oxidative esterification of the corresponding H-phosphonate analogues2008Inngår i: Collection Symposium Series, Vol. 10, 2008, s. 219-223Konferansepaper (Annet vitenskapelig)
  • 20.
    Bartoszewicz, Agnieszka
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kalek, Marcin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stawinski, Jacek
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    The case for the intermediacy of monomeric metaphosphate analogues during oxidation of H-phosphonothioate, H-phosphonodithioate, and H-phosphonoselenoate monoesters: mechanistic and synthetic studies2008Inngår i: The Journal of Organic Chemistry, ISSN 0022-3263, Vol. 73, nr 13, s. 5029-5038Artikkel i tidsskrift (Fagfellevurdert)
  • 21.
    Bartoszewicz, Agnieszka
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Livendahl, Madeleine
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient synthesis of beta-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates2008Inngår i: Chemistry: a European Journal, ISSN 0947-6539, Vol. 14, nr 34, s. 10547-10550Artikkel i tidsskrift (Fagfellevurdert)
  • 22.
    Bartoszewicz, Agnieszka
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Livendahl, Madeleine
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis of b-Hydroxy Ketones from Allylic Alcohols via Catalytic Formation of Ruthenium Enolates2008Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, nr 34, s. 10547-10550Artikkel i tidsskrift (Fagfellevurdert)
    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
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient and High-Yielding Routes to Diaryliodonium Salts2008Licentiatavhandling, med artikler (Annet vitenskapelig)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Aili, David
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Olofsson, Berit
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides2008Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, nr 12, s. 4602-4607Artikkel i tidsskrift (Fagfellevurdert)
    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
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Enantioselective Synthesis of Sec-Alcohol Derivatives and Diols via Combined Ruthenium and Enzyme Catalysis2008Doktoravhandling, med artikler (Annet vitenskapelig)
    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
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Oscarson, Stefan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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.2008Inngår i: Journal of Molecular Biology, ISSN 0022-2836, E-ISSN 1089-8638, Vol. 381, nr 3, s. 622-33Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Cumpstey, Ian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides2008Inngår i: Chemical Communications, ISSN 1359-7345, nr 10, s. 1246-1248Artikkel i tidsskrift (Fagfellevurdert)
  • 28.
    Cumpstey, Ian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Intramolecular aglycon delivery2008Inngår i: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 343, nr 10-11, s. 1553-1573Artikkel, forskningsoversikt (Annet vitenskapelig)
  • 29.
    Cumpstey, Ian
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Gehrke, Sebastian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Erfan, Sayeh
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Cribiù, Riccardo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Studies on the synthesis of valienamine and 1-epi-valienamine starting from D-glucose or L-sorbose2008Inngår i: Carbohydrate Research, ISSN 0008-6215, Vol. 343, nr 10-11, s. 1675-1692Artikkel i tidsskrift (Fagfellevurdert)
  • 30.
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Asymmetric amino acid catalysis2008Inngår i: Recent Devlopments in Physical Chemistry, 3rd Mexican Meeting on Mathematical and Experimental Physics, 2008, s. 47-59Konferansepaper (Fagfellevurdert)
  • 31.
    Córdova, Armando
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rios, Ramón
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Direct Catalytic Asymmetric Mannich Reactions and Surroundings2008Inngår i: Amino Group Chemistry. From Synthesis to the Life Sciences., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, s. 185-205Kapittel i bok, del av antologi (Fagfellevurdert)
  • 32. Dutheuil, Guillaume
    et al.
    Selander, Nicklas
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Szabó, Kálmán J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Aggarwal, Varinder K.
    Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts2008Inngår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 14, s. 2293-2297Artikkel i tidsskrift (Fagfellevurdert)
    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
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Asymmetric Organocatalytic Aldol and Mannich Reactions Catalyzed by Amino Acid-Derivatives and Small Peptides with a Primary Amine Functionality2008Licentiatavhandling, med artikler (Annet vitenskapelig)
  • 34.
    Dziedzic, Pawel
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ibrahem, Ismail
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives2008Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, nr 5, s. 803-807Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Vesely, Jan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready alpha-hydroxy-beta-amino acids2008Inngår i: Tetrahedron Letters, ISSN 0040-4039, Vol. 49, nr 47, s. 6631-6634Artikkel i tidsskrift (Fagfellevurdert)
    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
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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 activation2008Inngår i: Journal of Molecular Biology, ISSN 0022-2836, Vol. 376, nr 1, s. 109-119Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Widmalm, Göran
    Institutionen för organisk kemi.
    Methyl 3-O-alpha-D-mannopyranosyl beta-D-glucopyranoside tetrahydrate2008Inngår i: Acta Crystallographica Section E, ISSN 1600-5368, Vol. E64, nr 8, s. o1639-o1640Artikkel i tidsskrift (Fagfellevurdert)
  • 38.
    Frigell, Jens
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Towards Carbasugar-Based Mimics of Mycobacerial Arabinogalactan2008Licentiatavhandling, med artikler (Annet vitenskapelig)
  • 39.
    Färnbäck, Magnus
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Eriksson, Lars
    Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Methyl 2-O-beta-L-fucopyranosyl alpha-D-glucopyranoside monohydrate: a synchrotron study2008Inngår i: Acta Crystallographica Section C, ISSN 0108-2701, Vol. 64, nr 2, s. o31-o32Artikkel i tidsskrift (Fagfellevurdert)
  • 40. Gagliardo, Marcella
    et al.
    Selander, Nicklas
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mehendale, Nilesh C.
    van Koten, Gerard
    Klein Gebbink, Robertus J. M.
    Szabó, Kálmán J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes: synthesis and tandem catalytic activity of the first PCS-pincer palladium complex2008Inngår i: Chemistry: a European journal, ISSN 0947-6539, Vol. 14, nr 16, s. 4800-4809Artikkel i tidsskrift (Fagfellevurdert)
  • 41. Gao, Weiming
    et al.
    Liu, Jianhui
    Jiang, Weina
    Wang, Mei
    Weng, Linhong
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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 production2008Inngår i: Comptes Rendus Chimie, ISSN 1631-0748, Vol. 11, nr 8, s. 915-921Artikkel i tidsskrift (Fagfellevurdert)
  • 42. González, David
    et al.
    Grilló, María-Jesús
    De Miguel, María-Jesús
    Ali, Tara
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Arce-Gorvel, Vilma
    Delrue, Rose-May
    Conde-Álvarez, Raquel
    Munoz, Pilar
    López-Goni, Ignacio
    Iriarte, Maite
    Marín, Clara-M.
    Weintraub, Andrej
    Widmalm, Göran
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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 export2008Inngår i: PLoS ONE, ISSN 1932-6203, Vol. 3, nr 7, s. e2760 (1-15)Artikkel i tidsskrift (Fagfellevurdert)
  • 43. Gupta, Garima
    et al.
    Gemma, Emiliano
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Oscarson, Stefan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Surolia, Avadhesha
    Defining substrate interactions with calreticulin: an isothermal titration calorimetric study2008Inngår i: Glycoconjugate Journal, ISSN 0282-0080, Vol. 25, nr 8, s. 797-802Artikkel i tidsskrift (Fagfellevurdert)
  • 44. Hammar, Peter
    et al.
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Himo, Fahmi
    Density functional theory study of the stereoselectivity in small peptide-catalyzed intermolecular aldol reactions2008Inngår i: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 19, nr 13, s. 1617-1621Artikkel i tidsskrift (Fagfellevurdert)
  • 45.
    Hoben, Christine E.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kanupp, Lisa
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Practical chemoenzymatic dynamic kinetic resolution of primary amines via transfer of a readily removable benzyloxycarbonyl group2008Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, nr 6, s. 977-979Artikkel i tidsskrift (Fagfellevurdert)
  • 46.
    Híresová, Renáta
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Studies on Nucleotide Analogues Containing P-S-C Bond2008Licentiatavhandling, med artikler (Annet vitenskapelig)
  • 47.
    Ibrahem, Ismail
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hammar, Peter
    Vesely, Jan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rios, Ramón
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Eriksson, Lars
    Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Organocatalytic asymmetric hydrophosphination of alpha,beta-unsaturated aldehydes: Development, mechanism and DFT calculations2008Inngår i: Advanced Synthesis & Catalysis, ISSN 1615-4150, Vol. 350, nr 11-12, s. 1875-1884Artikkel i tidsskrift (Fagfellevurdert)
  • 48.
    Ibrahem, Ismail
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rios, Ramon
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Vesely, Jan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Zhao, Gui-Ling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Cordova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to beta-amino acids2008Inngår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 7, s. 1153-1157Artikkel i tidsskrift (Fagfellevurdert)
    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.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Zhao, Gui-Ling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rios, Ramón
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Vesely, Jan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sundén, Henrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Dziedzic, Pawel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    One-pot organocatalytic domino Michael/alpha-alkylation reactions: direct catalytic enantioselective cyclopropanation and cyclopentanation reactions2008Inngår i: Chemistry: a European journal, ISSN 0947-6539, Vol. 14, nr 26, s. 7867-7879Artikkel i tidsskrift (Fagfellevurdert)
  • 50.
    Johansson, Mikael
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Development of Biomimetic Catalytic Systems for Selective Oxidations with H2O2 and O22008Doktoravhandling, med artikler (Annet vitenskapelig)
    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.

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