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  • 1.
    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 B.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ryberg, Per
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    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 Enantioswitchability2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 42, p. 11197-11209Article in journal (Refereed)
    Abstract [en]

    Amino acid based thioamides, hydroxamic acids, and hydrazides have been evaluated as ligands in the rhodium-catalyzed asymmetric transfer hydrogenation of ketones in 2-propanol. Catalysts containing thioamide ligands derived from L-valine were found to selectively generate the product with an R configuration (95 % ee), whereas the corresponding L-valine-based hydroxamic acids or hydrazides facilitated the formation of the (S)-alcohols (97 and 91 % ee, respectively). The catalytic reduction was examined by performing a structure–activity correlation investigation with differently functionalized or substituted ligands and the results obtained indicate that the major difference between the thioamide and hydroxamic acid based catalysts is the coordination mode of the ligands. Kinetic experiments were performed and the rate constants for the reduction reactions were determined by using rhodium–arene catalysts derived from amino acid thioamide and hydroxamic acid ligands. The data obtained show that the thioamide-based catalyst systems demonstrate a pseudo-first-order dependence on the substrate, whereas pseudo-zero-order dependence was observed for the hydroxamic acid containing catalysts. Furthermore, the kinetic experiments revealed that the rate-limiting steps of the two catalytic systems differ. From the data obtained in the structure–activity correlation investigation and along with the kinetic investigation it was concluded that the enantioswitchable nature of the catalysts studied originates from different ligand coordination, which affects the rate-limiting step of the catalytic reduction reaction.

  • 2.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Fine-tuning catalytic activity and selectivity-[Rh(amino acid thioamide)] complexes for efficient ketone reduction2009In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, no 46, p. 6321-6324Article in journal (Refereed)
    Abstract [en]

    Amino acid-derived thioamides are prepared and evaluated as ligands in the rhodium-catalyzed asymmetric transfer hydrogenation of ketones in 2-propanol. It is found that increasing the steric bulk at the C-terminus of the ligand had a positive impact on both activity and selectivity in the reduction reaction. In order to find the optimum catalyst, a study is performed on a series of thioamide ligands having substituents of varying size.

  • 3.
    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-tosylimines: insights into the mechanism2009In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 351, no 16, p. 2657-2666Article in journal (Refereed)
    Abstract [en]

    The isomerisation of alkenols followed by reaction with aldehydes or N-tosylimines catalysed by rhodium complexes has been studied. The catalytically active rhodium complex is formed in situ from commercially available (cyclooctadiene)rhodium(l) chloride dimer [Rh(COD)Cl](2). The tandem process affords aldol and Mannich-type products in excellent yields. The key to the success of the coupling reaction is the activation of the catalysts by reaction with postassium tert-butoxide (t-BuOK), which promotes a catalytic cycle via alkoxides rather than rhodium hydrides. This mechanism minimises the formation of unwanted by-products. The mechanism has been studied by (1)H NMR spectroscopy and deuterium labelling experiments.

  • 4. Andersson, Samir
    et al.
    Zou, Dapeng
    Zhang, Rong
    Sun, Shiguo
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Selective positioning of CB[8] on two linked viologens and electrochemically driven movement of the host molecule2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 8, p. 1163-1172Article in journal (Refereed)
  • 5.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Larsson, Johanna M.
    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.
    Pincer complex-catalyzed redox coupling of alkenes with iodonium salts via presumed palladium(IV) intermediates2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 13, p. 2852-2854Article in journal (Refereed)
    Abstract [en]

    Palladium pincer complexes directly catalyze the redox coupling reactions of functionalized alkenes and iodonium salts. The catalytic process, which is suitable for mild catalytic functionalization of allylic acetates and electron-rich alkenes, probably occurs through Pd(IV) intermediates. Due to the strong metal−ligand interactions, the oxidation of phosphine and amine ligands of the pincer complexes can be avoided in the presented reactions.

  • 6.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Larsson, Johanna M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pincer Complex-Catalyzed Coupling Reactions via Palladium (IV) Intermediates2009In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 11, no 13, p. 2852-2854Article in journal (Refereed)
    Abstract [en]

    Palladium pincer complexes directly catalyze the redox coupling reactions of functionalized alkenes and iodonium salts. The catalytic process, which is suitable for mild catalytic functionalization of allylic acetates and electron-rich alkenes, probably occurs through Pd(IV) intermediates. Due to the strong metal−ligand interactions, the oxidation of phosphine and amine ligands of the pincer complexes can be avoided in the presented reactions.

  • 7.
    Ayesa, Susana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindquist, Charlotta
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Agback, Tatiana
    Benkestock, Kurt
    Classon, Björn
    Henderson, Ian
    Hewitt, Ellen
    Jansson, Katarina
    Kallin, Anders
    Sheppard, Dave
    Samuelsson, Bertil
    Solid-phase parallel synthesis and SAR of 4-amidofuran-3-one inhibitors of cathepsin S: Effect of sulfonamides P3 substituents on potency and selectivity.2009In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 17, no 3, p. 1307-1324Article in journal (Refereed)
    Abstract [en]

    Highly potent and selective 4-amidofuran-3-one inhibitors of cathepsin S are described. The synthesis and structure–activity relationship of a series of inhibitors with a sulfonamide moiety in the P3 position is presented. Several members of the series show sub-nanomolar inhibition of the target enzyme as well as an excellent selectivity profile and good cellular potency. Molecular modeling of the most interesting inhibitors describes interactions in the extended S3 pocket and explains the observed selectivity towards cathepsin K.

  • 8.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Building molecular complexity via tandem Ru-catalyzed isomerization/C-H activation2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 8, p. 1749-1752Article in journal (Refereed)
    Abstract [en]

    A tandem isomerization/C-H activation of allylic alcohols was performed using a catalytic amount of RUCl(2)(PPh(3))(3). A variety of ortho alkylated ketones have been obtained in excellent yields. This tandem process relies on an in situ generation of a carbonyl functional group that directs the ortho C-H bond activation.

  • 9.
    Bielawski, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient one-pot synthesis of bis(4-tert-butylphenyl)iodonium triflate2009In: Organic Syntheses, ISSN 0078-6209, Vol. 86, p. 308-314Article in journal (Refereed)
  • 10.
    Borén, Linnéa
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Leijondahl, Karin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic Kinetic Asymmetric Transformation of 1,4-diols and Preparation of Trans-2,5-Disubstituted pyrrolidines2009In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, no 26, p. 3237-3240Article in journal (Refereed)
    Abstract [en]

    Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,4-diols is carried out with Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and a ruthenium catalyst. A β-chloro-substituted 1,4-diol is successfully transformed into an optically pure 1,4-diacetate, which is a highly useful synthetic intermediate. The usefulness of the optically pure 1,4-diacetates is demonstrated by the synthesis of enantiopure 2,5-disubstituted pyrrolidines.

  • 11.
    Burkhardt, Anja
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    (Z)-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose O-benzyloxime2009In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. E65, no Part 3, p. o633-o633Article in journal (Refereed)
  • 12. Cribiù, Riccardo
    et al.
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    On the synthesis of vinyl and phenyl C-furanosides by stereospecific debenzylative cycloetherification2009In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 10, p. 2022-2031Article in journal (Refereed)
  • 13.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Alonzi, Dominic S.
    Butters, Terry D.
    Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis2009In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 344, no 4, p. 454-459Article in journal (Refereed)
  • 14.
    Córdova, Armando
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    The University of Barcelona, Departament Química Orgànica.
    Highly Z- and enantioselective ring-opening/cross-metathesis reactions and Z-selective ring-opening metathesis polymerization2009In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, no 47, p. 8827-8831Article in journal (Refereed)
  • 15. Daikoku, Shusaku
    et al.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kanie, Osamu
    Analysis of a series of isomeric oligosaccharides by energy-resolved mass spectrometry: a challenge on homobranched trisaccharides2009In: Rapid Communications in Mass Spectrometry, ISSN 0951-4198, E-ISSN 1097-0231, Vol. 23, no 23, p. 3713-3719Article in journal (Refereed)
  • 16.
    Deska, Jan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 17, p. 3379-3381Article in journal (Refereed)
  • 17.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Inorganic ammonium salts as catalysts for direct aldol reactions in the presence of water2009In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, no 52, p. 7242-7245Article in journal (Refereed)
  • 18.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schyman, Patric
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Physical 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 N-(phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 16, p. 4044-4048Article in journal (Refereed)
  • 19.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of carbadisaccharide mimics of galactofuranosides2009In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, no 36, p. 5142-5144Article in journal (Refereed)
  • 20.
    Gao, Yan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Liu, Jianhui
    Sun, Licheng
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nucleophilic attack of hydroxide on a MnV oxo complex: a model of the O-O bond formation in the oxygen evolving complex of photosystem II2009In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 131, no 25, p. 8726-8727Article in journal (Refereed)
  • 21. Georgieva, Polina
    et al.
    Wu, Qian
    McLeish, Michael J.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The reaction mechanism of phenylethanolamine N-methyltransferase: A density functional theory study2009In: Biochimica et Biophysica Acta, ISSN 0006-3002, E-ISSN 1878-2434, Vol. 1794, no 12, p. 1831-1837Article in journal (Refereed)
  • 22. Hernández-Toribio, Jorge
    et al.
    Gómez Arrayás, Ramón
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carretero, Juan C.
    Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with α,β-unsaturated ketones2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 2, p. 393-396Article in journal (Refereed)
  • 23.
    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.
    Lindberg, Staffan A.
    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 reoxidation of palladium by a hybrid catalyst in aerobic palladium-catalyzed carbocyclization of enallenes2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 28, p. 6799-6801Article in journal (Refereed)
  • 24.
    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 synthesis of hybrid (hydroquinone-Schiff base)cobalt oxidation catalysts2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 23, p. 3973-3976Article in journal (Refereed)
    Abstract [en]

    Hybrid catalysts A and B have recently been found to efficiently transfer electrons from a metal catalyst to molecular oxygen in biomimetic oxidations. In the present work hybrid catalysts A and B were synthesized in high yield from inexpensive starting materials. The key step is an efficient Suzuki cross-coupling, which allows the use of unprotected aldehyde 5. The new synthesis of the title hybrid catalysts is easy to carry out and can be scaled up.

  • 25.
    Jonsson, K. Hanna M.
    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 determination of the O-antigenic polysaccharide from Escherichia coli O742009In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 344, no 12, p. 1592-1595Article in journal (Refereed)
    Abstract [en]

    The structure of the O-antigen polysaccharide (PS) from Escherichia coli O74 has been determined. Component analysis, together with 1H and 13C NMR spectroscopy as well as 1H,15N-HSQC experiments were employed to elucidate the structure. Inter-residue correlations were determined by 1H,1H-NOESY and 1H,13C-heteronuclear multiple-bond correlation experiments. The PS is composed of tetrasaccharide repeating units with the following structure:

    Full-size image (5K)

    Cross-peaks of low intensity from an α-linked N-acetylglucosamine residue were present in the NMR spectra, and spectral analysis indicates that they originate from the penultimate residue in the polysaccharide. Consequently, the biological repeating unit has a 3-substituted N-acetyl-d-glucosamine residue at its reducing end. The 1H, 13C and 15N NMR chemical shifts of the α- and β-anomeric forms of d-Fucp3NAc are also reported. The repeating unit of the E. coli O74 O-antigen is identical to that of the capsular polysaccharide from E. coli K45.

  • 26.
    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.
    Preparation of arylphosphonates by palladium(0)-catalyzed cross-coupling in the presence of acetate additives: Synthetic and mechanistic studies2009In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 351, no 18, p. 3207-3216Article in journal (Refereed)
    Abstract [en]

    An efficient protocol for the synthesis of arylphosphonate diesters via a palladium-catalyzed cross-coupling of H-phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross-coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions were optimized in terms of amount of the catalyst, supporting ligands, and source of the acetate ion used. Various arylphosphonates, including those of potential biological significance, were synthesized using this newly developed protocol. Some mechanistic aspects of the investigated reactions are also discussed.

  • 27.
    Kalek, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient synthesis of mono-and diarylphosphinic acids: a microwave-assisted palladium-catalyzed cross-coupling of aryl halides with phosphinate2009In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 50, p. 10406-10412Article in journal (Refereed)
    Abstract [en]

    A general, efficient method for the microwave-assisted synthesis of mono- and diarylphosphinic acids from anilinium phosphinate and aryl halides, using Pd(0) and Xantphos as a supporting ligand, was developed.

  • 28.
    Karlsson, Erik A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oxidation of ethers, alcohols, and unfunctionalized hydrocarbons by the methyltrioxorhenium/H2O2 system: a computational study on catalytic C-H bond activation2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 8, p. 1862-1869Article in journal (Refereed)
    Abstract [en]

    A concerted mechanism that does not involve an ionic intermediate was revealed by a DFT study on oxidation of ethers, alcohols, and unfunctionalized hydrocarbons by methyltrioxorhenium/H2O2. Instead, CH insertion occurs through hydride transfer and then turns into a hydroxide transfer/rebound in a concerted fashion. The picture shows selected frames from an intrinsic reaction coordinate scan from the transition state to the product for the oxidation of cis-1,2-dimethylcyclohexane.

    The potential-energy surfaces (PESs) of methyltrioxorhenium (MTO)-catalyzed CH insertion reactions in the presence of hydrogen peroxide were studied by accurate DFT methods for a series of substrates including unsaturated hydrocarbons, an ether, and an alcohol. Based on the comprehensive analysis of transition states and intrinsic reaction coordinate (IRC) scans, CH insertion was found to proceed by a concerted mechanism that does not require, as previously thought, a side-on or a butterfly-like transition state. We found that a typical transition state follows requirements of the SN2 reaction instead. Furthermore, by exploring the PESs of several CH insertion reactions, we discovered that no ionic intermediate is formed even in a polar solvent. The latter was modeled within the self-consistent reaction field approach in a polarizable continuum model (PB-SCRF/PCM). According to our study, CH insertion occurs by a concerted but highly asynchronous mechanism that first proceeds by hydride transfer and then turns into hydroxide transfer/rebound. For the oxidation of alcohols, CH bond cleavage occurs without formation of alkoxide intermediates on the dominant pathway. The computed deuterium kinetic isotope effect of 2.9 for the hydride-transfer transition state for alcohol oxidation is in good agreement with the experimental kH/kD ration of 3.2 reported by Zauche and Espenson. As confirmed by IRC and PES scans in different solvents, the OH-rebound phase of the CH insertion pathway demonstrates strong similarities with the rebound mechanism that was previously proposed for cytochrome P450 and metalloporphyrin-catalyzed oxidations.

  • 29.
    Krumlinde, Patrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of a neonicotinoide pesticide derivative via chemoenzymatic dynamic kinetic resolution2009In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 74, no 19, p. 7407-7410Article in journal (Refereed)
  • 30.
    Lavén, Gaston
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium(0)-catalyzed benzylation of H-phosphonate diesters: An efficient entry to benzylphosphonates2009In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 2, p. 225-228Article in journal (Refereed)
    Abstract [en]

    A new, efficient method for the synthesis of benzylphosphonate diesters via a palladium(0)-catalyzed cross-coupling reaction between benzyl halides and H-phosphonate diesters, using Pd(OAc)2 as a palladium source and Xantphos as a supporting ligand, has been developed.

  • 31.
    Lavén, Gaston
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthetic studies on the preparation of nucleoside 5'-H-phosphonate monoesters under the Mitsunobu reaction conditions2009In: ARKIVOC, ISSN 1424-6376, no 3, p. 20-27Article in journal (Refereed)
    Abstract [en]

    A reaction of suitably protected nucleosides with phosphonic acid in the presence of diethyl azodicarboxylate and triphenylphosphine in pyridine provided in good yields the corresponding 5’-H-phosphonate monoesters.

  • 32.
    Leijondahl, Karin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borén, Linnéa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Braun, Roland
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enzyme- and ruthenium-catalyzed dynamic kinetic asymmetric transformation of 1,5-diols: Application to the synthesis of (+)-Solenopsin A2009In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 74, no 5, p. 1988-1993Article in journal (Refereed)
    Abstract [en]

    Dynamic kinetic asymmetric transformation (DYKAT) of 1,5-diols via combined lipase and ruthenium catalysis provides enantiomerically pure diacetates in high diastereoselectivity, which can serve as intermediates in natural product synthesis. This is demonstrated by the synthesis of (+)-Solenopsin A.

  • 33.
    Liao, Rong-Zhen
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yu, Jian-Guo
    Liu, Ruo-Zhuang
    Theoretical study of the RNA hydrolysis mechanism of the dinuclear zinc enzyme RNase Z2009In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, Vol. 2009, no 20, p. 2967-2972Article in journal (Refereed)
    Abstract [en]

    RNase Z is a dinuclear zinc enzyme that catalyzes the removal of the tRNA 3'-end trailer. Density functional theory is used to investigate the phosphodiester hydrolysis mechanism of this enzyme with a model of the active site constructed on the basis of the crystal structure. The calculations imply that the reaction proceeds through two steps. The first step is a nucleophihc attack by a bridging hydroxide coupled with protonation of the leaving group by a Glu-His diad. Subsequently, a water molecule activated by the same Glu-His diad makes a reverse attack, regenerating the bridging hydroxide. The second step is calculated to be the rate-limiting step with a barrier of 18 kcal/mol, in good agreement with experimental kinetic studies. Both zinc ions participate in substrate binding and orientation, facilitating nucleophilic attack. In addition, they act as electrophilic catalysts to stabilize the pentacoordinate trigonal-bipyramidal transition states.

  • 34.
    Liao, Rong-Zhen
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yu, Jian-Guo
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Reaction Mechanism of the Dinuclear Zinc Enzyme N-Acyl-l-homoserine Lactone Hydrolase: A Quantum Chemical Study2009In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 48, no 4, p. 1442-1448Article in journal (Refereed)
    Abstract [en]

    N-acyl-L-homosedne lactone hydrolase (AHL lactonase) is a dinuclear zinc enzyme responsible for the hydrolytic ring opening of AHLs, disrupting quorum sensing in bacteria. The reaction mechanism is investigated using hybrid density functional theory. A model of the active site is designed on the basis of the X-ray crystal structure, and stationary points along the reaction pathway are optimized and analyzed. Two possible mechanisms based on two different substrate orientations are considered. The calculations give support to a reaction mechanism that involves two major chemical steps: nucleophilic attack on the substrate carbonyl carbon by the bridging hydroxide and ring opening by direct ester C-O bond cleavage, The roles of the two zinc ions are analyzed. Zn1 is demonstrated to stabilize the charge of the tetrahedral intermediate, thereby facilitating the nucleophilic attack, while Zn2 stabilizes the charge of the alkoxide resulting from the ring opening, thereby lowering the barrier for the C-O bond cleavage.

  • 35.
    Merritt, Eleanor A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Malmgren, Joel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Klinke, Felix J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of diaryliodonium triflates using environmentally benign oxidizing agents2009In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 14, p. 2277-2280Article in journal (Refereed)
  • 36.
    Nozière, Barbara
    et al.
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM). Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Common inorganic ions are efficient catalysts for organic reactions in atmospheric aerosols and other natural environments2009In: Atmospheric Chemistry and Physics Discussion, Vol. 9, no 1, p. 1-21Article in journal (Other (popular science, discussion, etc.))
    Abstract [en]

    In this work, inorganic ammonium ions, NH4+, and carbonate ions, CO32-, are reported for the first time as catalysts for organic reactions in atmospheric aerosols and other natural environments at the Earth’s surface. These reactions include the formation of C-C and C-O bonds by aldol condensation and acetal formation, and reveal a new aspect of the interactions between organic and inorganic materials in natural environments. The catalytic properties of inorganic ammonium ions, in particular, were not previously known in chemistry. The reactions were found to be as fast in tropospheric ammonium sulfate composition as in concentrated sulfuric acid. The ubiquitous presence and large concentrations of ammonium ions in tropospheric aerosols would make of ammonium catalysis a main consumption pathway for organic compounds in these aerosols, while acid catalysis would have a minor contribution. In particular, ammonium catalysis would account quantitatively for the aging of carbonyl compounds into secondary “fulvic” compounds in tropospheric aerosols, a transformation affecting the optical properties of these aerosols. In general, ammonium catalysis is likely to be responsible for many observations previously attributed to acid catalysis in the troposphere.

  • 37.
    Nozière, Barbara
    et al.
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Products and Kinetics of the Liquid-Phase Reaction of Glyoxal Catalyzed by Ammonium Ions (NH4+)2009In: Journal of Physical Chemistry A, ISSN 1089-5639, Vol. 113, no 1, p. 231-237Article in journal (Refereed)
    Abstract [en]

    Glyoxal, a common atmospheric gas, has been reported to be depleted in some regions of the atmosphere. The corresponding sink could be accounted for by reactions in or at the surface of atmospheric particles, but these reactions were not identified. Recently, we showed that inorganic ammonium ions, NH4+, are efficient catalysts for reactions of carbonyl compounds, including glyoxal, in the liquid phase. To determine whether ammonium-catalyzed reactions can contribute to depletion of glyoxal in the atmosphere, the reactivity of this compound in aqueous solutions containing ammonium salts (ammonium sulfate, chloride, fluoride, and phosphate) at 298 K has been studied. The products identified by LC-HRMS and UV absorption revealed a mechanism involving two distinct pathways: a Bronsted acid pathway and an iminium pathway. The kinetics of the iminium pathway was studied by monitoring formation of a specific product. This pathway was second order in glyoxal in most of the solutions studied and should therefore be second order in most ammonium containing aerosols in the atmosphere. The corresponding rate constant, kII (M-1 s-1), increased strongly with ammonium ion activity, aNH4+, and pH:

    kII (M-1 s-1) ) (2 ( 1) × 10-10 exp(1.5 ( 0.8)aNH4+ exp(2.5 ( 0.2)pH.

    This iminium pathway is a lower limit for the ammonium-catalyzed consumption of glyoxal, but the contribution of the acid pathway is expected to be small in tropospheric aerosols. With these results the reactive uptake of glyoxal on ammonium-containing aerosols was estimated and shown to be a possible explanation for the depletion of this compound in Mexico City.

  • 38.
    Nyhlén, Jonas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    "Frustration" of orbital interactions in Lewis base/Lewis acid adducts: a computational study of H2 uptake by phosphanylboranes R2P=BR'22009In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 19, p. 2759-2764Article in journal (Refereed)
    Abstract [en]

    The reaction of mol. hydrogen with phosphanylboranes R2P:BR'2 (1) is systematically studied by d. functional theory calcns. and second order Moller-Plesset perturbation theory. The potential energy barriers and the exothermicity of H2 uptake are reported for a series of phosphanylboranes with different electron-donating and -withdrawing groups bound to phosphorus and boron. Systematic MO anal. reveals that the "frustration" between boron and phosphorus can be increased by modifying the substituents, and thus, AO interactions could be exploited in order to increase the reactivity of 1. Addnl., authors found a correlation between the potential energy barrier for H2 uptake and the energy of the HOMO of the P:B complex, which could be relevant for the prediction of the properties of candidate compds. for H2 activation and therefore useful for the development of such systems. [on SciFinder(R)]

  • 39.
    Nyhlén, Jonas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    On the possibility of catalytic reduction of carbonyl moieties with tris(pentafluorophenyl)borane and H2: a computational study2009In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, no 29, p. 5780-5786Article in journal (Refereed)
    Abstract [en]

    The study thoroughly examines the Gibbs free energy surfaces of a new mechanism for redn. of ketones/aldehydes by tris(pentafluorophenyl)borane (1) and H2. Key elements of the proposed mechanism are the proton and the hydride transfer steps similar to Stephan's catalytic redn. of imines by 1. The proton is transferred to the ketone/aldehyde in the process of H2 cleavage by the carbonyl-borane couple and the hydride is transferred in a nucleophilic attack on the carbonyl carbon by the hydridoborate in the ionic pair, [HOCRR']+[HB(C6F5)3]-. The in solvent Gibbs free energy barriers of H2 splitting by adducts of B(C6F5)3 with acetone, acetophenone and benzaldehyde are predicted to be in the range of 24.5 ± 2.5 kcal mol-1, which corresponds to potential energy barriers in the range of 17.0 ± 2.0 kcal mol-1. Significantly lower barrier of H2 activation is predicted in cases of bulky ketones such as 2,2,4,4-tetramethylpentan-3-one. With respect to the hydridoborate intermediate, the nucleophilic attack on the activated carbon is predicted to have a relatively low barrier for the sterically unhindered substrates, while this barrier is considerably higher for the sterically encumbered substrates. Since the formation of the hydridoborate intermediates is found to be endothermic, the transition state of the nucleophilic attack is the highest point of the computed energy profile for all tested substrates. Overall, according to in solvent d. function calcns. the proposed redn. of "compact" ketones/aldehydes by 1 and H2 is allowed both thermodynamically and kinetically at elevated temp., but it is expected to be slower and more substrate specific than the corresponding redn. of imines. [on SciFinder(R)]

  • 40.
    Nyhlén, Jonas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Racemization of alcohols catalyzed by [RuCl(CO)25-pentaphenylcyclopentadienyl)] – Mechanistic insights from theoretical modeling2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 21, p. 5220-5229Article in journal (Refereed)
    Abstract [en]

    Two possible pathways of inner-sphere racemization of sec-alcohols by using the [RuCl(CO)(2)(eta(5)-pentaphenylcyclopentadienyl)] catalyst (1) have been thoroughly investigated by means of density function calculations. To be able to racemize alcohols, catalyst 1 needs to have a free coordination site on the metal. This can be achieved either by a eta(5)-->eta(3) ring slippage or by dissociation of a carbon monoxide (CO) ligand. The eta(5)-->eta(3) ring-slip pathway was found to have a high potential energy barrier, 42 kcal mol(-1), which can be explained by steric congestion in the transition state. On the other hand, CO dissociation to give a 16-electron complex has a barrier of only 22.6 kcal mol(-1). We have computationally discovered a mechanism involving CO participation that does not require eta(5)-->eta(3) ring slippage. The key features of this mechanism are 1) CO-assisted exchange of chloride for alkoxide, 2) alcohol-alkoxide exchange, and 3) generation of an active 16-electron complex through CO dissociation with subsequent beta-hydride elimination as the racemization step. We have found a low-energy pathway for reaction of 1 with potassium tert-butoxide and a pathway for fast alkoxide exchange with interaction between the incoming/leaving alcohol and one of the two CO ligands. We predict that dissociation of a Ru-bound CO ligand does not occur in these exchange reactions. Dissociation of one of the two Ru-bound CO ligands has been found necessary only at a later stage of the reaction. Though this barrier is still quite high, our results indicate that it is not necessary to cross the CO dissociation barrier for the racemization of each new alcohol. Thus, the dissociation of a CO ligand is interpreted as a rate-limiting reaction step in order to create a catalytically active 16-electron complex.

  • 41.
    Olsson, Johan D M
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Landström, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rönnols, Jerk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 8, p. 1612-1618Article in journal (Refereed)
  • 42.
    Olsson, Johan D M
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures2009In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 20, no 6/8, p. 879-886Article in journal (Refereed)
  • 43.
    Olsson, Ulrika
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Säwén, Elin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stenutz, Roland
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Conformational flexibility and dynamics of two (1→6)-linked disaccharides related to an oligosaccharide epitope expressed on malignant tumour cells2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 35, p. 8886-8894Article in journal (Refereed)
    Abstract [en]

    The conformational flexibility and dynamics of two (1→6)-linked disaccharides that are related to the action of the glycosyl transferase GnT-V have been investigated. NMR NOE and T-ROE spectroscopy experiments, conformation-dependent coupling constants and molecular dynamics (MD) simulations were used in the analyses. To facilitate these studies, the compounds were synthesised as α-d-[6-13C]-Manp-OMe derivatives, which reduced the 1H NMR spectral overlap and facilitated the determination of two- and three-bond 1H,1H, 1H,13C and 13C,13C-coupling constants. The population distribution for the glycosidic ω torsion angle in α-d-Manp-(1→6)-α-d-Manp-OMe for gt/gg/tg was equal to 45:50:5, whereas in α-d-Manp-OMe it was determined to be 56:36:8. The dynamic model that was generated for β-d-GlcpNAc-(1→6)-α-d-Manp-OMe by MD simulations employing the PARM22/SU01 CHARMM-based force field was in very good agreement with experimental observations. β-d-GlcpNAc-(1→6)-α-d-Manp-OMe is described by an equilibrium of populated states in which the ϕ torsion angle has the exo-anomeric conformation, the ψ torsion angle an extended antiperiplanar conformation and the ω torsion angle a distribution of populations predominantly between the gauchetrans and the gauchegauche conformational states (i.e., gt/gg/tg) is equal to 60:35:5, respectively. The use of site-specific 13C labelling in these disaccharides leads to increased spectral dispersion, thereby making NMR spectroscopy based conformational analysis possible that otherwise might be difficult to attain.

  • 44.
    Olsson, Vilhelm J.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Functionalization of unactivated alkenes through iridium-catalyzed borylation of carbon-hydrogen bonds. Mechanism and synthetic applications.2009In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 74, no 20, p. 7715-7723Article in journal (Refereed)
  • 45.
    Persson, Andreas K. Å.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Copper-catalyzed N-allenylation of allylic sulfonamides2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 17, p. 3814-3817Article in journal (Refereed)
    Abstract [en]

    Allylic allenic amides have been synthesized via a copper-catalyzed cross-coupling between allylic sulfonamides and bromoallenes in moderate to good yields. Copper(I) thiophene-2-carboxylate (CuTC) was used a source of copper with DMEDA as the ligand. The allenylated products obtained are potential substrates for palladium-catalyzed carbocyclizations.

  • 46.
    Pilarski, Lukasz T.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Böse, Dietrich
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic allylic C—H acetoxylation and benzoyloxylation via suggested (η3-allyl)palladium(IV) intermediates2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 23, p. 5518-5521Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed allylic acetoxylations and benzoyloxylations were carried out using iodonium salts. The reactions proceed under mild conditions with high regio- and stereoselectivity. The catalysis can be performed under both acidic and nonacidic conditions without use of BQ or other external oxidants and activator ligands. Deuterium labeling experiments clearly show that the catalytic reaction proceeds through (η3-allyl)palladium intermediates. A stoichiometric study with one of the catalysts provided evidence for the formation of a Pd(IV) species.

  • 47.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hydrogenation of imines by phosphonium borate zwitterions: a theoretical study2009In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. -, no 8, p. 1321-1327Article in journal (Refereed)
  • 48.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    On the possibility of conversion of alcohols to ketones and aldehydes by phosphinoboranes R2PBR'R'': a computational study2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 8, p. 1825-1829Article in journal (Refereed)
  • 49.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The role of amine-B(C6F5)3 adducts in the catalytic reduction of imines with H2: a computational study2009In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 15, p. 2229-2237Article in journal (Refereed)
  • 50.
    Privalov, Timofei
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Boschloo, Gerrit
    Hagfeldt, Anders
    Svensson, Per H.
    Kloo, Lars
    A study of the interactions between I-/I3- redox , mediators amd organometallic sensitizing dyes in solar cells2009In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 113, no 2, p. 783-790Article in journal (Refereed)
12 1 - 50 of 71
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