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  • 301.
    Fransson, Ann-Britt L.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Xu, Yongmei
    Leijondahl, Karin
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enzymatic Resolution, Desymmetrization and Dynamic Kinetic Asym-metric Transformation of 1,3-Cycloalkanediols2006In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, no 17, p. 6309-6316Article in journal (Refereed)
    Abstract [en]

    An efficient desymmetrization of cis-1,3-cyclohexanediol to (1S,3R)-3-(acetoxy)-1-cyclohexanol ((R,S)-2a) was performed via Candida antarctica lipase B (CALB)-catalyzed transesterification, in high yield (up to 93%) and excellent enantioselectivity (ee's up to >99.5%). (R,R)-Diacetate ((R,R)-3a) was obtained in a DYKAT process at room temperature from (1S,3R)-3-acetoxy-1-cyclohexanol ((R,S)-2a), in a high trans/cis ratio (91:9) and in excellent enantioselectivity of >99%. Metal- and enzyme-catalyzed dynamic transformation of cis/trans-1,3-cyclohexanediol using PS-C gave a high diastereoselectivity for cis-diacetate (cis/trans = 97:3). The (1R,3S)-3-acetoxy-1-cyclohexanol (ent-(R,S)-2a) was obtained from cis-diacetate by CALB-catalyzed hydrolysis in an excellent yield (97%) and selectivity (>99% ee). By deuterium labeling it was shown that intramolecular acyl migration does not occur in the transformation of cis-monoacetate to the cis-diacetate.

  • 302. Fransson, Ann-Britt
    et al.
    Xu, Yongmei
    Leijondahl, Karin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Enzymatic resolution, desymmetrization and dynamic kinetic asymmetric transformation of 1,3-cycloalkanediols2006In: Journal of organic chemistry, ISSN 0022-3263, Vol. 71, no 17, p. 6309-6316Article in journal (Refereed)
  • 303.
    Franzén, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carbon-Carbon bond formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbozyclization of Allene-Substituted Olefins2003In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, no 20, p. 6056-6057Article in journal (Refereed)
  • 304.
    Franzén, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Löfstedt, Joakim
    Dorange, Ismet
    Bäckvall, Jan E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions: Observation of anti Attack of Allenes on (p-Allyl)Palladium Complexes2002In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 124, no 38, p. 11246-11247Article in journal (Refereed)
  • 305.
    Franzén, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Löfstedt, Joakim
    Falk, Jennica
    Bäckvall, Jan-E
    Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates.2003In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, no 46, p. 14140-14148Article in journal (Refereed)
  • 306. François, Camille
    et al.
    Pourchet, Sylvie
    Boni, Gilles
    Rautiainen, Sari
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samec, Joseph
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Fournier, Lucie
    Robert, Carine
    Thomas, Christophe M.
    Fontaine, Stephane
    Gaillard, Yves
    Placet, Vincent
    Plasseraud, Laurent
    Design and synthesis of biobased epoxy thermosets from biorenewable resources2017In: Comptes rendus. Chimie, ISSN 1631-0748, E-ISSN 1878-1543, Vol. 20, no 11-12, p. 1006-1016Article in journal (Refereed)
    Abstract [en]

    Biobased diepoxy synthons derived from isoeugenol, eugenol or resorcinol (DGE-isoEu, DGE-Eu and DGER, respectively) have been used as epoxy monomers in replacement of the diglycidyl ether of bisphenol A (DGEBA). Their curing with six different biobased anhydride hardeners leads to fully biobased epoxy thermosets. These materials exhibit interesting thermal and mechanical properties comparable to those obtained with conventional petrosourced DGEBA-based epoxy resins cured in similar conditions. In particular, a high T-g in the range of 90-130 degrees C and instantaneous moduli higher than 4.3 GPa have been recorded. These good performances are very encouraging, making these new fully biobased epoxy thermosets compatible with the usual structural application of epoxy materials.

  • 307.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carbasugar analogues of galactofuranosides: alpha-O-linked derivatives2010In: BEILSTEIN J ORG CHEM, ISSN 1860-5397, Vol. 6, p. 1127-1131Article in journal (Refereed)
    Abstract [en]

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

  • 308.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    First synthesis of 4a-carba-beta-D-galactofuranose2007In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, no 52, p. 9073-9076Article in journal (Refereed)
  • 309.
    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)
  • 310.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carbasugar analogues of galactofuranosides: beta-O-linked derivatives and towards beta-S-linked derivatives2011In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 346, no 11, p. 1277-1290Article in journal (Refereed)
    Abstract [en]

    A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether.

  • 311.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pearcey, Jean A.
    Lowary, Todd L.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carbasugar Analogues of Galactofuranosides: Pseudodisaccharide Mimics of Fragments of Mycobacterial Arabinogalactan2011In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 7, p. 1367-1375Article in journal (Refereed)
    Abstract [en]

    A partially protected carbasugar analogue of beta-galactofuranose was converted into an alpha-galacto-configured 1,2-epoxide, which was opened by alcohols under Lewis acid catalysis with regioselective attack at C-1 to give beta-galacto-configured C-1 ethers. Using OH-5 and OH-6 carbagalactofuranose derivatives as nucleophiles, we synthesised pseudodisaccharide analogues of substructures of the arabinogalactan from M. tuberculosis. The dicarba analogue of the disaccharide Galf(beta 1 -> 5) Galf was found to moderately inhibit the action of GlfT2 galactofuranosyl transferase from M. tuberculosis.

  • 312.
    Fryxelius, Jacob
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eilers, Gerriet
    Feyziyev, Yashar
    Magnuson, Ann
    Sun, Licheng
    Lomoth, Reiner
    Synthesis and redox properties of a [meso-tris(4-nitrophenyl)corrolato]Mn(III) complex2005In: Journal of Porphyrins and Phtalocyanines, Vol. 9, p. 379-386Article in journal (Refereed)
  • 313.
    Fryxelius, Jacob
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pica, Delphine
    Eriksson, Lars
    Åkermark, Björn
    Preparation of Copper(II) Complexes of a Mixed Amide-Phenolate LigandIn: Inorganic Chemistry CommunicationsArticle in journal (Refereed)
  • 314.
    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)
  • 315.
    Färnbäck, Magnus
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Söderman, Peter
    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 3,4,6-tri-O-acetyl-2-deoxy-2-azido-alpha-D-galactopyranosyl-(1-2)-: [3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl-(1-3)]-4-O-benzoyl-alpha-L-rhamnopyranoside n-hexane 0.1-solvate2007In: Acta Crystallographica: Section E, Vol. E63, p. o1581-o1583Article in journal (Refereed)
  • 316. 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)
  • 317.
    Galkin, Maxim V.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Smit, Arjan T.
    Subbotina, Elena
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Artemenko, Konstantin A.
    Bergquist, Jonas
    Huijgen, Wouter J. J.
    Samec, Joseph S. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hydrogen-free catalytic fractionation of woody biomass2016In: ChemSusChem, ISSN 1864-5631, E-ISSN 1864-564X, Vol. 9, no 23, p. 3280-3287Article in journal (Refereed)
    Abstract [en]

    The pulping industry could become a biorefinery if the lignin and hemicellulose components of the lignocellulose are valorized. Conversion of lignin into well-defined aromatic chemicals is still a major challenge. Lignin depolymerization reactions often occur in parallel with irreversible condensation reactions of the formed fragments. Here, we describe a strategy that markedly suppresses the undesired condensation pathways and allows to selectively transform lignin into a few aromatic compounds. Notably, applying this strategy to woody biomass at organosolv pulping conditions, the hemicellulose, cellulose, and lignin were separated and in parallel the lignin was transformed into aromatic monomers. In addition, we were able to utilize a part of the lignocellulose as an internal source of hydrogen for the reductive lignin transformations. We hope that the presented methodology will inspire researchers in the field of lignin valorization as well as pulp producers to develop more efficient biomass fractionation processes in the future.

  • 318. Gao, Weiming
    et al.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Jianhui
    Chen, Changneng
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Weng, Linhong
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Binuclear iron-sulfur complexes with bidentate phosphine ligands as active site models of Fe-hydrogenase and their catalytic proton reduction2007In: Inorganic Chemistry, ISSN 0020-1669, Vol. 46, no 6, p. 1981-1991Article in journal (Refereed)
  • 319. 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)
  • 320. Gao, Weiming
    et al.
    Liu, Jianhui
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Bidentate phosphine ligand based Fe2S2-containing macromolecules: synthesis, characterization, and catalytic electrochemical hydrogen production2006In: Inorganic Chemistry, ISSN 0020-1669, Vol. 45, no 23, p. 9169-9171Article in journal (Refereed)
  • 321. Gao, Weiming
    et al.
    Liu, Jianhui
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Facile and highly efficient light-induced PR3/CO ligand exchange: a novel approach to the synthesis of [(mu-SCH2NnPrCH2S)Fe2(CO)4(PR3)2]2007In: Journal of Organometallic Chemistry, ISSN 0022-328X, Vol. 692, p. 1579-1583Article in journal (Refereed)
  • 322.
    Gao, Weiming
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Li, Mingrun
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Romare, Kristina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Royal Institute of Technology (KTH), Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of a [3Fe2S] cluster with low redox potential from [2Fe2S] hydrogenase models: electrochemical and photochemical generation of hydrogen2011In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, Vol. 2011, no 7, p. 1100-1105Article in journal (Refereed)
    Abstract [en]

    In the attempted replacement of carbon monoxide by the bis(phosphane) dppv in a dinuclear [2Fe2S] complex, a trinuclear [3Fe2S] complex with two bis(phosphane) ligands was unexpectedly obtained. On protonation, this gave a bridged hydride complex with an unusually low potential for the reduction of protons to molecular hydrogen. The redox potential also appears sufficiently positive for direct electron transfer from an excited [Ru(bpy)(3)](2+) sensitizer.

  • 323.
    Gao, Weiming
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Åkermark, Torbjörn
    Li, Mingrun
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Sun, Licheng
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Attachment of a hydrogen-bonding carboxylate side chain to an [FeFe]-hydrogenase model complex: Influence on the catalytic mechanism2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 8, p. 2537-2546Article in journal (Refereed)
    Abstract [en]

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

  • 324.
    Gao, Yan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Jianhui
    Jiang, Wenfeng
    Xia, Ming
    Zhang, Wei
    Li, Minna
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Synthesis and photophysical and electrochemical properties of a binuclear Ru(bpy)3-Cu(III) corrole complex2007In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, Vol. 11, no 5-6, p. 463-469Article in journal (Refereed)
  • 325. Gao, Yan
    et al.
    Liu, Jianhui
    Na, Yong
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Synthesis and characterization of manganese and copper corrole xanthene complexes as catalysts for water oxidation2007In: Tetrahedron, ISSN 0040-4020, Vol. 63, no 9, p. 1987-1994Article in journal (Refereed)
  • 326.
    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)
  • 327.
    Gemma, Emiliano
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lahmann, Martina
    Oscarson, Stefan
    Synthesis of the tetrasaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp recognised by Calreticulin/Calnexin2005In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 340, no 16, p. 2558-2562Article in journal (Refereed)
    Abstract [en]

    The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.

  • 328. George, Riham F.
    et al.
    Ismail, Nasser S. M.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Girgis, Adel S.
    Design, synthesis and QSAR studies of dispiroindole derivatives as new antiproliferative agents2013In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 68, p. 339-351Article in journal (Refereed)
    Abstract [en]

    A variety of 4'-ary1-3-(arylmethylidene)-1 ''-[(cyclic-amino)methylene]-1'-methyl-dispiro[cyclohexane-1,3'-pyrrolidine-2',3 ''-[3H]indole]-2,2 ''(1H)-diones 4a-u were prepared via reaction of 2E,6E-bis(arylidene)-1-cyclohexanones 1a-i with azomethine ylides, generated in situ via a decarboxylative condensation of isatins 2a-c and sarcosine (3). Single crystal X-ray study of 4a, revealed structural and stereochemical features of these derivatives. While most of the synthesized compounds exhibit mild antitumor properties when tested against various human tumor cell lines (HEPG2 liver, HELA cervical and PD prostate cancers), three of them, 4d and 4p (active against HEPG2), and compound 4g (active against HELA), demonstrated higher activities, that were close or even higher than that of the reference standard Doxorubicin. QSAR studies revealed good predictive and statistically significant 3 descriptor models (r(2) = 0.903-0.812, r(adjusted)(2) = 0.855-0.672, r(prediction)(2) = 0.773-0.605).

  • 329.
    Georgieva, Polina
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Quantum chemical modeling of enzymatic reactions: The Case of histone lysine methyltransferase2010In: Journal of Computational Chemistry, ISSN 0192-8651, E-ISSN 1096-987X, Vol. 31, no 8, p. 1707-1714Article in journal (Refereed)
    Abstract [en]

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

  • 330. 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)
  • 331. Ghanem, Raed
    et al.
    Xu, Yunhua
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    pan, Jie
    Hoffmann, Tobias
    Andersson, Johan
    Polivka, Tomas
    Pascher, Torbjörn
    Styring, Stenbjörn
    Sun, Licheng
    Sundström, Villy
    Light-driven Tyrosine Radical Formation in a Ruthenium-Tyrosine Complex Attached to Nanoparticle TiO22002In: Inorganic Chemistry, ISSN 0020-1669, Vol. 41, no 24, p. 6258-6266Article in journal (Refereed)
  • 332. Ghobril, Cynthia
    et al.
    Hammar, Peter
    Kodepelly, Sanjeevarao
    Spiess, Bernard
    Wagner, Alain
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Baati, Rachid
    Structure-Reactivity Relationship Studies for Guanidine-Organocatalyzed Direct Intramolecular Aldolization of Ketoaldehydes2010In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 2, no 12, p. 1573-1581Article in journal (Refereed)
    Abstract [en]

    Structure-reactivity studies are performed to explore the reaction mechanism of the guanidine-catalyzed intramolecular aldol reaction of ketoaldehydes. A large number of guanidine and guanidine-like catalysts are synthesized and their properties studied. Kinetic profiles and pK(a) values of the catalysts are measured and correlated to reaction barriers calculated using density functional theory (DFT). The DFT calculations show that structural rigidity influences the pKa of the guanidines. Although the basicity is a very important factor in the catalysis, it is not sufficient to fully account for its catalytic efficiency. The availability of two aligned nitrogen reaction sites for proton shuttling in the transition state is an essential feature that helps to rationalize the reactivity pattern and the activation mode for this family of organocatalysts.

  • 333.
    Ghosh, Raju
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Room Temperature, Metal-Free Arylation of Aliphatic Alcohols2014In: ChemistryOpen, ISSN 2191-1363, Vol. 3, no 2, p. 54-57Article in journal (Refereed)
    Abstract [en]

    Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal-free conditions. The reaction proceeds at room temperature within 90min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron-withdrawing substituents are transferred most efficiently, and unsymmetric iodonium salts give chemoselective arylations. The methodology has been applied to the formal synthesis of butoxycaine.

  • 334.
    Ghosh, Raju
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Metal-Free Synthesis of N-Aryloxyimides and Aryloxyamines2014In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 6, p. 1830-1832Article in journal (Refereed)
    Abstract [en]

    N-Hydroxyphthalimide and N-hydroxysuccinimide have been arylated with diaryliodonium salts to provide N-aryloxyimides in excellent yields in short reaction times. A novel hydrolysis under mild and hydrazine-free conditions yielded aryloxyamines, which are valuable building blocks in the synthesis of oxime ethers and benzofurans.

  • 335.
    Ghosh, Raju
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stridfeldt, Elin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Metal-Free One-Pot Synthesis of Benzofurans2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 29, p. 8888-8892Article in journal (Refereed)
    Abstract [en]

    Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B.

  • 336.
    Gigant, Nicolas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Conjugated Dienes via a Biomimetic Aerobic Oxidative Coupling of Two CvinylH Bonds2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 33, p. 10799-10803Article in journal (Refereed)
    Abstract [en]

    A time to dienes: A highly efficient and general method has been developed to prepare conjugated dienes through a biomimetic approach. This aerobic oxidative coupling, involving two CvinylH bonds, proceeds under low Pd catalyst loading and employs catalytic amounts of p-benzoquinone and iron phthalocyanine as electron-transfer mediators (ETMs) under ambient oxygen pressure (see scheme).

  • 337.
    Gigant, Nicolas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Access to Cinnamyl Derivatives from Arenes and Allyl Esters by a Biomimetic Aerobic Oxidative Dehydrogenative Coupling2014In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 6, p. 1664-1667Article in journal (Refereed)
    Abstract [en]

    An efficient biomimetic aerobic oxidative dehydrogenative alkenylation of arenes with allyl esters is presented. The reaction proceeds under an ambient pressure of oxygen with relatively low catalyst loading of palladium acetate, employing catalytic amounts of electron-transfer mediators (ETMs). This study represents a new environmentally friendly method for the synthesis of cinnamyl derivatives.

  • 338.
    Gigant, Nicolas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aerobic Direct C-H Arylation of Nonbiased Olefins2014In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 17, p. 4432-4435Article in journal (Refereed)
    Abstract [en]

    An efficient ligand-promoted biomimetic aerobic oxidative dehydrogenative cross-coupling between arenes and nonbiased olefins is presented. Acridine as a ligand was found to significantly enhance the rate, the yield, and the scope of the reaction under ambient oxygen pressure, providing a variety of alkenylarenes via an environmentally friendly procedure.

  • 339.
    Gigant, Nicolas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aerobic Double Dehydrogenative Cross Coupling between Cyclic Saturated Ketones and Simple Arenes2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 20, p. 5890-5894Article in journal (Refereed)
    Abstract [en]

    The synthesis of 3-aryl-2-cyclohexenones is a topic of current interest as they are not only privileged structures in bioactive molecules, but they are also relevant feedstocks for the synthesis of substituted phenols or anilines, which are ubiquitous structural elements both in drug design and medicinal chemistry. A simple and sustainable one-pot aerobic double dehydrogenative reaction under mild conditions for the introduction of arenes in the -position of cyclic ketones has been developed. Starting from the corresponding saturated ketone, this reaction sequence proceeds under relatively low Pd catalyst loading and involves catalytic amounts of electron-transfer mediators (ETMs) under ambient oxygen pressure.

  • 340.
    Gigant, Nicolas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Université Paris-Sud, France.
    Quintin, Francois
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Preparation of Tetrasubstituted Olefins Using Mono or Double Aerobic Direct C-H Functionalization Strategies: Importance of Steric Effects2015In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, no 5, p. 2796-2803Article in journal (Refereed)
    Abstract [en]

    A novel protocol for the synthesis of tetrasubstituted olefins through a biomimetic approach has been explored. Both mono- and diarylations were performed under ambient oxygen pressure, giving a range of highly hindered tetrasubstituted alkenes. For diarylation of disubstituted substrates, it was demonstrated that the second arylation is the rate-limiting step of the overall transformation.

  • 341. Girgis, Adel S.
    et al.
    Mabied, Ahmed F.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hegazy, Lamees
    George, Riham F.
    Farag, Hanaa
    Shalaby, ElSayed M.
    Farag, I. S. Ahmed
    Synthesis and DFT studies of an antitumor active spiro-oxindole2015In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 39, no 10, p. 8017-8027Article in journal (Refereed)
    Abstract [en]

    An anti-oncological active spiro-oxindole 7 was synthesized regioselectively via a [3+2]-cycloaddition reaction of azomethine ylide to exocyclic olefinic linkage of 4-piperidone 6, exhibiting properties against diverse tumor cell lines including leukemia, melanoma and cancers of the lung, colon, brain, ovary, breast, prostate, and kidney. Compound 7 crystallizes in the monoclinic system and P21/c space group with four molecules in the unit cell. The structure was also studied by AM1, PM3 and DFT techniques. DFT studies support the stereochemical selectivity of the reaction and determine the molecular electrostatic potential and frontier molecular orbitals.

  • 342. Girgis, Adel S.
    et al.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ismail, Nasser S. M.
    Farag, Hanaa
    Synthesis and QSAR study of novel cytotoxic spiro[3H-indole-3,2 '(1 ' H)-pyrrolo[3,4-c]pyrrole]-2,3 ',5 '(1H,2 ' aH,4 ' H)-triones2012In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 47, p. 312-322Article in journal (Refereed)
    Abstract [en]

    1,3-Dipolar cycloaddition reaction of 1-aryl-1H-pyrrole-2,5-diones 1a-e with non-stabilized azomethine ylides, generated in situ via decarboxylative condensation of isatins 2a-c and sarcosine (3) in refluxing ethanol, afforded 4'-aryl-5'a,6'-dihydro-1'-methyl-spiro[3H-indole-3,2'(1 ' H)-pyrrolo[3,4-c]pyrrole]-2,3',5'(1H,2'aH,4'H)-triones 4a-o in good yields. Compound 4I exhibited high anti-tumor activity against HEPG2 (liver cancer) cell line (IC50 = 12.16 mu M) compared to that of Doxorubicin (IC50= 7.36 mu M), and the other synthesized compounds revealed moderate anti-tumor properties against HCT116 (colon), MCF7 (breast) and HEPG2 (liver) human tumor cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explore the structural requirements controlling the observed anti-tumor properties. It was found that the major structural factors affecting potency of these compounds were related to their basic skeleton.

  • 343. Godefroid, Marie
    et al.
    Svensson, Mona V
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cambier, Pierre
    Uzureau, Sophie
    Mirabella, Aurélie
    De Bolle, Xavier
    Van Cutsem, Pierre
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Letesson, Jean-Jacques
    Brucella melitensis 16M produces a mannan and other extracellular matrix components typical of a biofilm2010In: FEMS Immunology and Medical Microbiology, ISSN 0928-8244, E-ISSN 1574-695X, Vol. 59, no 3, p. 364-377Article in journal (Refereed)
  • 344.
    Goncalves, Sylvie
    et al.
    Universite de Strasbourg, Faculte de Pharmacie UMR/CNRS 7199, Laboratoire des Systemes Chimiques Fonctionnels, Illkirch, France.
    Santoro, Stefano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nicolas, Marc
    Les Laboratoires Pierre Fabre, Centre de Developpement Chimique et Industriel, Gaillac, France.
    Wagner, Alain
    Universite de Strasbourg, Faculte de Pharmacie UMR/CNRS 7199, Laboratoire des Systemes Chimiques Fonctionnels, Illkirch, France.
    Maillos, Philippe
    Les Laboratoires Pierre Fabre, Centre de Developpement Chimique et Industriel, Gaillac, France.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Baati, Rachid
    Universite de Strasbourg, Faculte de Pharmacie UMR/CNRS 7199, Laboratoire des Systemes Chimiques Fonctionnels, Illkirch, France.
    Cationic cyclization of 2-alkenyl-1,3-dithiolanes: DiastereoselectiveSynthesis of trans-decalins2011In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 9, p. 3274-3285Article in journal (Refereed)
    Abstract [en]

    An unprecedented and highly diastereoselective 6-endo-trig cyclization of 2-alkenyl-1,3-dithiolanes has beendeveloped yielding trans-decalins, an important scaffold present in numerous di- and triterpenes. The novelty of this 6-endo-trigc yclization stands in the stepwise mechanism involving 2-alkenyl-1,3-dithiolane, acting as a novel latent initiator. It is suggested that the thioketal opens temporarily under the influence of TMSOTf, triggering the cationic 6-endo-trig cyclization, andcloses after C−C bond formation and diastereoselective protonation to terminate the process. DFT calculations confirm this mechanistic proposal and provide a rationale for the observed diastereoselectivity. The reaction tolerates a wide range of functionalities and nucleophilic partners within the substrate. We have also shown that the one-pot 6-endo-trig cyclization followedby in situ 1,3-dithiolane deprotection afford directly the corresponding ketone. This improvement allowed the achievement of the shortest total synthesis of triptophenolide and the shortest formal synthesis of triptolide.

  • 345. 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)
  • 346.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nonclassical cyclodehydration of diols assisted by metal-ligand cooperation2017Article in journal (Refereed)
  • 347.
    González Miera, Greco
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chupas, Peter J.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chapman, Karena W.
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Topological Transformation of a Metal–Organic Framework Triggered by Ligand Exchange2017In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 56, no 8, p. 4576-4583Article in journal (Refereed)
    Abstract [en]

    Here we describe the topological transformation of the pores of a new framework in the bio-MOF-100 family (dia-c) into the known isomer (lcs) by doubling the pore volume, which occurs during postsynthesis modifications. During this transformation, reassembling of the metal–organic framework (MOF) building blocks into a completely different framework occurs, involving breaking/forming of metal–ligand bonds. MOF crystallinity and local structure are retained, as determined by powder X-ray diffraction (PXRD) and pair distribution function (PDF) analyses, respectively. We exploited the inherent dynamism of bio-MOF-100 by coupling chemical decorations of the framework using solvent-assisted ligand exchange to the topological change. Following this method and starting from the pristine dense dia-c phase, open lcs-bio-MOF-100 was prepared and functionalized in situ with an iridium complex (IrL). Alternatively, the dia-c MOF could be modified with wide-ranging amounts of IrL up to ca. 50 mol %, as determined by solution 1H NMR spectroscopy, by tuning the concentration of the solutions used and with no evidence for isomer transformation. The single-site nature of the iridium complexes within the MOFs was assessed by X-ray absorption spectroscopy (XAS) and PDF analyses. Ligand exchanges occurred quantitatively at room temperature, with no need of excess of the iridium metallolinker.

  • 348.
    González Miera, Greco
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    López, Aitor Bermejo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Norrby, Per-Ola
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex2019In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 10, p. 2631-2636Article in journal (Refereed)
    Abstract [en]

    1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)-Ir-III complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

  • 349.
    González Miera, Greco
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Acceptorless Alcohol Dehydrogenation: OH vs NH Effect in Bifunctional NHC–Ir(III) Complexes2018In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 37, no 5, p. 636-644Article in journal (Refereed)
    Abstract [en]

    Bifunctional complexes bearing N-heterocyclic carbene (NHC) ligands functionalized with hydroxy or amine groups were synthesized to measure the beneficial effect of different modes of metal–ligand cooperation in the acceptorless dehydrogenation of alcohols. In comparison to complexes with an amine moiety, hydroxy-functionalized iridium catalysts showed superior activity. In contrast to alcohols, 1,4-diols underwent cyclization to give the corresponding tetrahydrofurans without involving dehydrogenation processes. Mechanistic investigations to rationalize the “OH effect” in these types of complexes have been undertaken.

  • 350. Goulart, Paula N.
    et al.
    da Silva, Clarissa O.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The importance of orientation of exocyclic groups in a naphthoxyloside: A specific rotation calculation study2017In: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, Vol. 30, no 12, article id e3708Article in journal (Refereed)
    Abstract [en]

    2-Naphthyl -d-xylopyranoside (XylNap) inhibits -1,4-galactosyltransferase 7 (4GalT7) and thereby growth of tumor cells both in vitro and in vivo. The binding pocket of 4GalT7 has a defined orientation of hydrogen bond acceptors and hydrophobic moiety. Knowing the orientation of the hydroxyl and naphthyl groups of this molecule would help in the development of more efficient inhibitors. In this work, we have tried, for the first time, to determine the exocyclic hydroxyl and aglycon groups orientation of XylNap, using ab initio descriptions, and calculation of the specific rotation values, in methanol solutions, using 2 different solvent descriptions: a dielectric continuum approach (polarizable continuum model [PCM]) and a microsolvated+continuum approach (MS+PCM). In the PCM approach, [](D)=-59 deg/(dm(g/cm(3))) whereas for the MS+PCM approach [](D)=-29 deg/(dm(g/cm(3))). The latter is in excellent agreement with the experimentally determined value in methanol solution, viz, [](D)=-30 deg/(dm(g/cm(3))). This agreement allows us to say that the hydroxyl groups have similar orientations in xylose and XylNap, and the naphthyl group has a very well-defined dihedral angle value in the most abundant conformations.

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