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  • 1. Ahlberg, P.
    et al.
    Karlsson, A.
    Goeppert, A.
    Lill, S. O. N.
    Dinér, P.
    Sommer, J.
    Solvated CH5+ in liquid superacid2001In: Chemistry-a European Journal, Vol. 7, no 9, p. 1936-1943Article in journal (Refereed)
    Abstract [en]

    The transition states for methane activation in liquid superacid have been studied by experimentally determined secondary kinetic deuterium isotope effects (SKIEs) and computational chemistry. For the first time, the SKIEs on hydrogen/deuterium exchange of methane have been measured by using the methane isotopologues in homogeneous liquid superacid ((HF)-H-2/ SbF5). To achieve high accuracy of the SKIEs, the rate constants for pairs of methane isotopologues were simultaneously measured in the same superacid solution by using NMR spectroscopy Density functional theory (DFT and high-level ab initio methods have been employed to model possible intermediates and transition states, assuming that the superacids involved in the exchange reactions are H2F- ions solvated by HF Only the unsolvated superacid H2F- is found to be strong enough to protonate methane. yielding the methonium ion solvated by HF as a potential energy minimum. In contrast, the (HF)(x)-solvated H2F- superacids (x = 1-4) do not appear to be strong enough to yield stable solvated methonium ions. However, such ions show up as parts of the transition slates of the exchange in which the methonium ions are solvated by (HF)(x). The calculated DFT activation barrier is in good agreement with that experimentally observed.

  • 2. Ahlberg, P.
    et al.
    Karlsson, A.
    Goeppert, A.
    Lill, S. O. N.
    Dinér, P.
    Sommer, J.
    Solvated CH5+ in liquid superacid (vol 7, pg 1936, 2001)2001In: Chemistry-a European Journal, Vol. 7, no 12, p. 2501-2501Article in journal (Refereed)
  • 3. Amorati, Riccardo
    et al.
    Valgimigli, Luca
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Bakhtiari, Khadijeh
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Saeedi, Mina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Multi-faceted reactivity of alkyltellurophenols towards peroxyl radicals: Catalytic antioxidant versus thiol-depletion effect2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 23, p. 7510-7522Article in journal (Refereed)
    Abstract [en]

    Hydroxyaryl alkyl tellurides are effective antioxidants both in organic solution and aqueous biphasic systems. They react by an unconventional mechanism with ROO. radicals with rate constants as high as 107M1s1 at 303K, outperforming common phenols. The reactions proceed by oxygen atom transfer to tellurium followed by hydrogen atom transfer to the resulting RO. radical from the phenolic OH. The reaction rates do not reflect the electronic properties of the ring substituents and, because the reactions occur in a solvent cage, quenching is more efficient when the OH and TeR groups have an ortho arrangement. In the presence of thiols, hydroxyaryl alkyl tellurides act as catalytic antioxidants towards both hydroperoxides (mimicking the glutathione peroxidases) and peroxyl radicals. The high efficiency of the quenching of the peroxyl radicals and hydroperoxides could be advantageous under normal cellular conditions, but pro-oxidative (thiol depletion) when thiol concentrations are low.

  • 4. Bertelsen, Søren
    et al.
    Dinér, Peter
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Johansen, Rasmus Lyng
    Jørgensen, Karl Anker
    Asymmetric organocatalytic beta-hydroxylation of alpha, beta-unsaturated aldehydes2007In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129, no 6, p. 1536-1537Article in journal (Refereed)
    Abstract [en]

    The first catalytic enantioselective beta-hydroxylation of alpha,beta-unsaturated aldehydes is presented. Using commercially available (E)-benzaldehyde oxime in the presence of 2-[bis(3,5-bis-trifluoromethyl-phenyl)trimethyl-silanyloxymethyl]pyrrolidine as organocatalyst, the corresponding chiral carbonyl beta-oxime ethers are obtained in high yields and with excellent enantioselectivities. These optically active carbonyl and hydroxy beta-oxime ethers are highly interesting biological compounds in, e.g., sex pheromone analogues, highly potent antiinflammatory agents, and penicillin and cephalosporin analogues. The chiral carbonyl beta-oxime ethers can be reduced to the corresponding 1,3-diols in high yields. Furthermore, the organocatalytic enantioselective beta-hydroxylation of alpha,beta-unsaturated aldehydes could be performed on gram scale without loss of enantioselectivity.

  • 5. Bertelsen, Søren
    et al.
    Marigo, Mauro
    Brandes, Sebastian
    Dinér, Peter
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Jørgensen, Karl Anker
    Dienamine catalysis: organocatalytic asymmetric gamma-amination of alpha,beta-unsaturated aldehydes2006In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, no 39, p. 12973-12980Article in journal (Refereed)
    Abstract [en]

    A new concept in organocatalysis is presented, the direct asymmetric gamma-functionalization of alpha,beta-unsaturated aldehydes. We disclose that secondary amines can invert the usual reactivity of alpha,beta-unsaturated aldehydes, enabling a direct gamma-amination of the carbonyl compound using azodicarboxylates as the electrophilic nitrogen-source. The scope of the reaction is demonstrated for the enantioselective gamma-amination of different alpha,beta-unsaturated aldehydes, giving the products in moderate to good yields and with high enantioselectivities up to 93% ee. Experimental investigations and DFT calculations indicate that the reaction might proceed as a hetero-Diels-Alder cycloaddition reaction. Such a mechanism can explain the "unexpected" stereochemical outcome of the reaction.

  • 6. Dierckx, Anke
    et al.
    Dinér, Peter
    University of Gothenburg.
    El-Sagheer, Afaf H
    Kumar, Joshi Dhruval
    Brown, Tom
    Grøtli, Morten
    Wilhelmsson, L Marcus
    Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA.2011In: Nucleic Acids Research, ISSN 0305-1048, E-ISSN 1362-4962, Vol. 39, no 10, p. 4513-24Article in journal (Refereed)
    Abstract [en]

    To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA. A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, A(T) shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that A(T) only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that A(T) shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

  • 7.
    Dinér, P.
    et al.
    University of Gothenburg.
    Andersson, T.
    University of Gothenburg.
    Kjellén, J.
    University of Gothenburg.
    Elbing, K.
    University of Gothenburg.
    Hohmann, S.
    University of Gothenburg.
    Grotli, M.
    University of Gothenburg.
    Short cut to 1,2,3-triazole-based p38 MAP kinase inhibitors via [3+2]-cycloaddition chemistry2009In: New Journal of Chemistry, Vol. 33, no 5, p. 1010-1016Article in journal (Refereed)
    Abstract [en]

    A series of 4,5-substituted 1,2,3-triazoles was synthesised via Cu(I)-catalysed azide-alkyne 1,3-dipolar [2 + 3]-cycloaddition reactions followed by a Suzuki coupling. The 1,2,3-triazoles were evaluated as inhibitors of the p38 alpha MAP kinase, showing IC50 values in the high nanomolar range.

  • 8.
    Dinér, P.
    et al.
    University of Gothenburg.
    Pettersen, D.
    University of Gothenburg.
    Nilsson Lill, S. O.
    University of Gothenburg.
    Ahlberg, P.
    University of Gothenburg.
    Investigation of site selectivity of the stereoselective deprotonation of cyclohexene oxide using kinetic resolution of isotopic enantiomers in natural abundance2005In: Tetrahedron-Asymmetry, Vol. 16, no 15, p. 2665-2671Article in journal (Refereed)
    Abstract [en]

    Stereo selective deprotonation of epoxides with lithium arnides can occur by abstraction of protons from more than one site. The site selectivity of the deprotonation of cyclohexene oxide by several chiral and achiral lithium amides has been investigated. H-2 NMR has been used to measure the relative abundances of the isotopomers of the epoxide containing one deuterium. An isotopic stereoisomer, with deuterium in the site undergoing abstraction, reacts slower than its enantiomer and other isotopomers having protium in the same site due to a kinetic isotope effect. This results in a kinetic resolution yielding a relative excess of the less reactive isotopic stereoisomer. Thus, the relative abundance of such an enantiomer increases when compared with those having protium at the site in question as the reaction proceeds. It can be concluded that deprotonation of cyclohexene oxide using some chiral- and non-chiral lithium amides occurs by beta syn-deprotonation. (c) 2005 Elsevier Ltd. All rights reserved.

  • 9.
    Dinér, P
    et al.
    University of Gothenburg.
    Vilg, J VUniversity of Gothenburg.Kjellen, JUniversity of Gothenburg.Iwona, MUniversity of Wroclaw.Andersson, TUniversity of Gothenburg.Hohmann, SUniversity of Gothenburg.Wysocki, RUniversity of Wroclaw .Tamas, M JUniversity of Gothenburg.Grotli, MUniversity of Gothenburg.
    Design, synthesis and characterization of a highly effective Hog1 inhibitor: a powerful tool for analyzing MAP kinase signaling in yeast2010Conference proceedings (editor) (Other academic)
  • 10.
    Dinér, Peter
    Department of Chemistry, University of Gothenburg.
    Alkane activation by superacids and enantioselective reactions with chiral lithium amides: computational and experimental mechanistic studies2005Doctoral thesis, comprehensive summary (Other academic)
  • 11.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Catalytic asymmetric chiral lithium amide-promoted epoxide rearrangement: a NMR spectroscopic and kinetic investigation2010In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, no 21-22, p. 2733-2739Article in journal (Refereed)
    Abstract [en]

    The lithium amide derived from the chiral diamine (1R,3S,4S)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane, has been reported to catalytically deprotonate cyclohexene oxide and other epoxides, yielding chiral allylic alcohols in excellent enantiomeric excess. In this work, 6Li, 1H and 13 C NMR spectroscopy have been used to study the aggregation of the chiral lithium amide in THF and the influence on the aggregation by the addition of additives, such as 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU). The activated complex under catalytic deprotonation of cyclohexene oxide, that is, with excess Li-DBU and free DBU, is built from one monomer of the chiral lithium amide, one molecule of epoxide and one additional molecule of DBU. The reaction order (0.97) obtained for the bulk base Li-DBU shows an inverse dependence on the concentration, suggesting a deaggregation of the initial mixed dimer to a monomer-based transition state containing a monomer of the lithium amide.

  • 12.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Superacid-Promoted Ionization of Alkanes Without Carbonium Ion Formation: A Density Functional Theory Study2012In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 116, no 40, p. 9979-9984Article in journal (Refereed)
    Abstract [en]

    The carbonium ion has been suggested to be the intermediate in superacid-promoted reactions (SbF5-HF) such as hydrogen-deuterium exchange and in the electrophilic C-H cleavage into hydrogen and the carbenium ion. In this study, the superacid-promoted C-H cleavage into hydrogen and the carbenium ion was studied using density functional theory (B3LYP and M062X) and ab initio methods (MP2 and CCSD). The calculations suggest that the superacid-promoted C-H cleavage proceeds via a concerted transition state leading to hydrogen (H-2) and the carbenium ion without the formation of the elusive carbonium ion. The reactivity for the superacid promoted C-H cleavage decreases upon going from isobutane (tertiary) > propane (secondary) > isobutane (primary) > propane (primary) > ethane >> methane.

  • 13.
    Dinér, Peter
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Alao, John P.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Söderlund, Johan
    Sunnerhagen, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Grøtli, Morten
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Preparation of 3-Substituted-1-Isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines as RET Kinase Inhibitors2012In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 55, no 10, p. 4872-4876Article in journal (Refereed)
    Abstract [en]

    A series of 3-substituted-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines have been designed, synthesized, and evaluated as RET protein kinase inhibitors. On the basis of docking results, a small library of pyrazolopyrimidine compounds with an extended hydrophobic side arm was synthesized. The most promising of the compounds (7a) displayed efficient inhibition in vitro and good selectivity when tested on a panel of kinases. Furthermore, 7a inhibited GDNF-induced RET phosphorylation of ERK1/2 in MCF-7 breast cancer cells at concentrations as low as 100 nM.

  • 14.
    Dinér, Peter
    et al.
    Organic Chemistry, Department of Chemistry, Göteborg University.
    Amedjkouh, Mohamed
    Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases2006In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, no 11, p. 2091-2096Article in journal (Refereed)
    Abstract [en]

    Chiral alpha-aminophosphonates have been synthesized and their performance was evaluated as organocatalysts in the direct asymmetric aldol reaction. High enantioselectivities (up to 99% ee) were achieved for a range of substituted cyclohexanones and benzaldehydes. Several organic bases, such as DBU, DBN, and TMG, were used together with the alpha-aminophosphonates in the aldol reactions and were found to favor syn-selectivity.

  • 15.
    Dinér, Peter
    et al.
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Kjaersgaard, Anne
    Lie, Mette Alstrup
    Jørgensen, Karl Anker
    On the origin of the stereoselectivity in organocatalysed reactions with trimethylsilyl-protected diarylprolinol2008In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 1, p. 122-127Article in journal (Refereed)
    Abstract [en]

    The origin of the enantioselectivity in the TMS-protected (TMS=trimethylsilyl) prolinol-catalysed alpha-heteroatom functionalisation of aldehydes has been investigated by using density functional theory calculations. Eight different reaction paths have been considered which are based on four different conformers of the TMS-protected prolinol-enamine intermediate. Optimisation of the enamine structures gave two intermediates with nearly the same energy. These intermediates both have an E configuration at the C==C bond and the double bond is positioned anti or syn, relative to the 2-substituent in the pyrrolidine ring. For the four intermediates, the chiral TMS-protected-diaryl substituent effectively shields one of the faces of the reacting C==C bond in the enamine intermediate. A number of transition states have been calculated for the enantioselective fluorination by N-fluorobenzenesulfonimide (NFSI) and based on the transition-state energies it has been found that the enantioselectivity depends on the orientation of the C==C bond, being anti or syn, relative to the 2-substituent on the pyrrolidine ring, rather than the approach of the electrophilic fluorine to the face of the reacting carbon atom in the enamine which is less shielded relative to the face with the highest shielding. The calculated enantiomeric excess of 96 % ee (ee=enantiomeric excess) for the fluorination reaction corresponds well with the experimentally found enantiomeric excess-97 % ee. The transition state for the alpha-amination reaction with the same type of intermediate has also been calculated by using diethyl azodicarboxylate as the amination reagent. The implication of the intermediate structures on the stereoselection of alpha-functionalisation of aldehydes is discussed.

  • 16.
    Dinér, Peter
    et al.
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Nielsen, Martin
    Bertelsen, Søren
    Niess, Barbara
    Jørgensen, Karl Anker
    Enantioselective hydroxylation of nitroalkenes: an organocatalytic approach2007In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 35, p. 3646-3648Article in journal (Refereed)
    Abstract [en]

    An easy hydroxylation of aliphatic nitroalkenes in high yields and enantioselectivities is catalysed by bifunctional thiourea-cinchona alkaloids giving access to optically active nitroalcohols and aminoalcohols as final products.

  • 17.
    Dinér, Peter
    et al.
    Center for Catalysis Department of Chemistry, Aarhus University.
    Nielsen, Martin
    Marigo, Mauro
    Jørgensen, Karl Anker
    Enantioselective organocatalytic conjugate addition of N heterocycles to alpha,beta-unsaturated aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, no 12, p. 1983-1987Article in journal (Refereed)
  • 18.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Veide Vilg, Jenny
    Kjellén, Jimmy
    Migdal, Iwona
    Andersson, Terese
    Gebbia, Marinella
    Giaever, Guri
    Nislow, Corey
    Hohmann, Stefan
    Wysocki, Robert
    Tamás, Markus J.
    Grøtli, Morten
    Design, Synthesis, and Characterization of a Highly Effective Hog1 Inhibitor: A Powerful Tool for Analyzing MAP Kinase Signaling in Yeast2011In: PLoS ONE, Vol. 6, no 5, p. e20012-Article in journal (Refereed)
    Abstract [en]

    The Saccharomyces cerevisiaeHigh-Osmolarity Glycerol (HOG) pathway is a conserved mitogen-activated protein kinase (MAPK) signal transduction system that often serves as a model to analyze systems level properties of MAPK signaling. Hog1, the MAPK of the HOG-pathway, can be activated by various environmental cues and it controls transcription, translation, transport, and cell cycle adaptations in response to stress conditions. A powerful means to study signaling in living cells is to use kinase inhibitors; however, no inhibitor targeting wild-type Hog1 exists to date. Herein, we describe the design, synthesis, and biological application of small molecule inhibitors that are cell-permeable, fast-acting, and highly efficient against wild-type Hog1. These compounds are potent inhibitors of Hog1 kinase activity both in vitroand in vivo. Next, we use these novel inhibitors to pinpoint the time of Hog1 action during recovery from G1 checkpoint arrest, providing further evidence for a specific role of Hog1 in regulating cell cycle resumption during arsenite stress. Hence, we describe a novel tool for chemical genetic analysis of MAPK signaling and provide novel insights into Hog1 action.

  • 19.
    Dyrager, C.
    et al.
    University of Gothenburg.
    Börjesson, K.
    Chalmers University of Technology.
    Dinér, P.
    University of Gothenburg.
    Elf, A.
    University of Gothenburg.
    Albinsson, B.
    Chalmers University of Technology.
    Wilhelmsson, L. M.
    Chalmers University of Technology.
    Grotli, M.
    University of Gothenburg.
    Synthesis and Photophysical Characterisation of Fluorescent 8-(1H-1,2,3-Triazol-4-yl)adenosine Derivatives2009In: European Journal of Organic Chemistry, no 10, p. 1515-1521Article in journal (Refereed)
    Abstract [en]

    A series of 8-(1H-1,2,3-triazol-4-yl)-substituted adenosine derivatives have been synthesised by using Sonogashira cross-coupling and click chemistry. The use of click chemistry enables an easy access to different substituents in the 4-position of the triazole ring. The modified nucleosides show high absorptivities due to a single strongly allowed electronic transition and, for some of the derivatives, high quantum yields in organic as well as in water solution making them promising as fluorescent probes in nucleic acid contexts. Furthermore, the different substituents of the 1,2,3-triazole makes the wavelength of emission tunable without changing the absorption properties substantially. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  • 20.
    Dyrager, Christine
    et al.
    University of Gothenburg.
    Nilsson Möllers, Linda
    University of Gothenburg.
    Kjäll, Linda Karlsson
    University of Gothenburg.
    Alao, John Patrick
    University of Gothenburg.
    Diner, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Wallner, Fredrik
    University of Gothenburg.
    Sunnerhagen, Per
    University of Gothenburg.
    Grøtli, Morten
    University of Gothenburg.
    Design, Synthesis and Biological Evaluation of Chromone-based p38 MAP Kinase Inhibitors2011In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 54, no 20, p. 7427-7431Article in journal (Refereed)
    Abstract [en]

    A series of 3-(4-fluorophenyl)-2-(4-pyridyl)-chromone derivs. were synthesized and evaluated as p38 MAP kinase inhibitors. Introduction of an amino group in the 2-position of the pyridyl moiety gave p38 inhibitors with IC50 values in the low nanomolar range (e.g. 8a; IC50 = 17 nm). Addnl., the inhibitors (8a and 8e) demonstrate an excellent selectivity profile towards the p38 kinase among other kinases, as well as inhibition (8e) of p38 signaling in human breast cancer cells. [on SciFinder(R)]

  • 21.
    Díaz-Álvarez, Alba E.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Mesas Sanchez, Laura
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Non-Enzymatic Dynamic Kinetic Resolution of Secondary Aryl Alcohols: Planar Chiral Ferrocene and Ruthenium Catalysts in Cooperation2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 2, p. 502-504Article in journal (Refereed)
  • 22.
    Díaz-Álvarez, Alba E.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Mesas-Sánchez, Laura
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Nichtenzymatische dynamische kinetische Racematspaltung sekundärer Arylalkohole: planar-chirale Ferrocen- und Rutheniumkatalysatoren im Zusammenspiel2013In: Angewandte Chemie, ISSN 1521-3757, Vol. 125, no 2, p. 522-524Article in journal (Refereed)
  • 23. Goeppert, Alain
    et al.
    Dinér, Peter
    Organic Chemistry Department of Chemistry Göteborg University.
    Ahlberg, Per
    Sommer, Jean
    Methane activation and oxidation in sulfuric acid2002In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 8, no 14, p. 3277-3283Article in journal (Refereed)
    Abstract [en]

    The H/D exchange observed when methane is contacted with D(2)SO(4) at 270-330 degrees C shows that the alkane behaves as a sigma base and undergoes rapid and reversible protonation at this temperature. DFT studies of the hydrogen exchange between a monomer and a dimer of sulfuric acid and methane show that the transition states involved in the exchange are bifunctional, that is one hydrogen atom is transferred from a hydroxy group in sulfuric acid to methane, while one hydrogen atom is abstracted from methane by a non-hydroxy oxygen atom in sulfuric acid. All the transition states include a CH(5) moiety, which shows similarities to the methanium ion CH(5) (+). The calculated potential activation energy of the hydrogen exchange for the monomer is 174 kJ mol(-1), which is close to the experimental value (176 kJ mol(-1)). Solvation of the monomer and the transition state of the monomer with an extra sulfuric acid molecule, decrease the potential activation energy by 6 kJ mol(-1). The acid-base process is in competition, however, with an oxidative process involving methane and sulfuric acid which leads to CO(2), SO(2), and water, and thus to a decrease of acidity and loss of reactivity of the medium.

  • 24. Hamngren, C.
    et al.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Synthetical Organic Chemistry.
    Grøtli, M.
    Goksör, M.
    Adiels, C. B.
    Design and evaluation of a microfluidic system for inhibition studies of yeast cell signaling2012In: Proceedings of SPIE: The International Society for Optical Engineering, 2012, p. 84582K-Conference paper (Refereed)
    Abstract [en]

    In cell signaling, different perturbations lead to different responses and using traditional biological techniques that result in averaged data may obscure important cell-to-cell variations. The aim of this study was to develop and evaluate a four-inlet microfluidic system that enables single-cell analysis by investigating the effect on Hog1 localization post a selective Hog1 inhibitor treatment during osmotic stress. Optical tweezers was used to position yeast cells in an array of desired size and density inside the microfluidic system. By changing the flow rates through the inlet channels, controlled and rapid introduction of two different perturbations over the cell array was enabled. The placement of the cells was determined by diffusion rates flow simulations. The system was evaluated by monitoring the subcellular localization of a fluorescently tagged kinase of the yeast "High Osmolarity Glycerol" (HOG) pathway, Hog1-GFP. By sequential treatment of the yeast cells with a selective Hog1 kinase inhibitor and sorbitol, the subcellular localization of Hog1-GFP was analysed on a single-cell level. The results showed impaired Hog1-GFP nuclear localization, providing evidence of a congenial design. The setup made it possible to remove and add an agent within 2 seconds, which is valuable for investigating the dynamic signal transduction pathways and cannot be done using traditional methods. We are confident that the features of the four-inlet microfluidic system will be a valuable tool and hence contribute significantly to unravel the mechanisms of the HOG pathway and similar dynamic signal transduction pathways.

  • 25. Klein, Michael
    et al.
    Dinér, Peter
    Department of Chemistry, University of Gothenburg.
    Dorin-Semblat, Dominique
    Doerig, Christian
    Grøtli, Morten
    Synthesis of 3-(1,2,3-triazol-1-yl)- and 3-(1,2,3-triazol-4-yl)-substituted pyrazolo[3,4-d]pyrimidin-4-amines via click chemistry: potential inhibitors of the Plasmodium falciparum PfPK7 protein kinase2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 17, p. 3421-3429Article in journal (Refereed)
    Abstract [en]

    Efficient routes to 3-(1,2,3-triazol-1-yl)- and 3-(1,2,3-triazol-4-yl)pyrazolo[3,4-d]pyrimidin-4-amines using a one-pot two-step reaction are presented. The two routes give easy access to two different isomers of 1,4-disubstituted triazoles and the target compounds are obtained from a variety of readily available aromatic and aliphatic halides without isolation of potentially unstable organic azide intermediates. Two compounds show activity towards the PfPK7 kinase (IC(50) 10-20 microM) of P. falciparum, the organism responsible for the most virulent form of malaria, and can be regarded as hits useful for further development into lead compounds.

  • 26. Klein, Michael
    et al.
    Krainz, Karin
    Redwan, Itedale Namro
    Dinér, Peter
    Department of Chemistry, Medicinal Chemistry, University of Gothenburg.
    Grøtli, Morten
    Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids2009In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 14, no 12, p. 5124-5143Article in journal (Refereed)
    Abstract [en]

    A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues.

  • 27.
    Mesas-Sanchez, Laura
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Diaz-Alvarez, Alba E.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Koukal, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Diner, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst2014In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, no 24, p. 3807-3811Article in journal (Refereed)
    Abstract [en]

    Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee).

  • 28.
    Mesas-Sánchez, Laura
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Díaz-Álvarez, Alba Estrella
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 2, p. 753-757Article in journal (Refereed)
    Abstract [en]

    Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee).

  • 29.
    Nielsen, M
    et al.
    Aarhus University.
    Bertelsen, SAarhus University.Dinér, PAarhus University.Johansen, R LAarhus University.Niess, BAarhus University.Jorgensen, K AAarhus University.
    ORGN 703-Two diverse approaches for asymmetric organocatalytic beta-hydroxylation of alpha,beta-unsaturated electrophiles2008Conference proceedings (editor) (Other academic)
  • 30.
    Nielsen, M
    et al.
    Aarhus University.
    Dinér, PAarhus University.Jiang, HAarhus University.Zhuang, WAarhus University.Bertelsen, SAarhus University.Marigo, MAarhus University.Nielsen, J BAarhus University.Niess, BAarhus University.Jorgensen, K AAarhus University.
    ORGN 12-Asymmetric organocatalytic heteroatomic alpha- and beta-functionalizations of alpha,beta-unsaturated electrophiles2008Conference proceedings (editor) (Other academic)
  • 31.
    Nillsson Lill, S. O.
    et al.
    University of Gothenburg.
    Dinér, P.
    University of Gothenburg.
    Pettersen, D.
    University of Gothenburg.
    Amedjkouh, M.
    University of Gothenburg.
    Ahlberg, P.
    University of Gothenburg.
    Development of chiral catalysts for stereoselective synthesis by deprotonations - Experimentation in interplay with computational chemistry2004In: Advances in Quantum Chemistry, Vol. 47, p. 1-22Article in journal (Other academic)
    Abstract [en]

    Results are presented advancing the application of quantum chemistry in the field of organic synthesis. Computational chemistry in interplay with experimental chemistry has been given a key role in the development of stereoselective synthesis. Novel molecular systems are being created for catalytic stereoselective deprotonations, a reaction type useful for synthesizing many new compounds, e.g., some having important biological activities. Problems met in this approach to design catalysts and their solutions are presented.

  • 32.
    Pettersen, D.
    et al.
    University of Gothenburg.
    Dinér, P.
    University of Gothenburg.
    Amedjkouh, M.
    University of Gothenburg.
    Ahlberg, P.
    University of Gothenburg.
    Composition and structure of activated complexes in stereoselective deprotonation of cyclohexene oxide by a mixed dimer of chiral lithium amide and lithiated imidazole2004In: Tetrahedron-Asymmetry, Vol. 15, no 10, p. 1607-1613Article in journal (Refereed)
    Abstract [en]

    Stereoselective deprotonation of cyclohexene oxide, using a mixed dimer built of the chiral lithium amide, lithium (1R,2S)-N-methyl-1-phenyl-2-pyrrolidinyl-propanamide, and 2-lithio-1-methylimidazole, has been studied. The composition of the rate limiting activated complex was determined by kinetics to be built from one mixed dimer molecule and one epoxide molecule. Based on this knowledge computational chemistry has been applied to gain insight into possible structures of the activated complexes. (C) 2004 Elsevier Ltd. All rights reserved.

  • 33.
    Poon, Jia-Fei
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Alao, John Patrick
    Sunnerhagen, Per
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Azastilbenes: a cut-off to p38 MAPK inhibitors2013In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, no 27, p. 4526-4536Article in journal (Refereed)
    Abstract [en]

    Inhibitors with vicinal 4-fluorophenyl/4-pyridine rings on a five- or six-membered heterocyclic ring are known to inhibit the p38 mitogen-activated protein kinase (MAPK), which is a potential target for rheumatoid arthritis and several different types of cancer. Several substituted azastilbene-based compounds with vicinal 4-fluorophenyl/4-pyridine rings were designed using computational docking, synthesized, and evaluated in a cell-free radiometric p38[small alpha] assay. The biochemical evaluation shows that the best inhibition (down to 110 nM) is achieved for azastilbene-based compounds having an isopropylamine substituent in the 2-position of the pyridine ring. The inhibition of p38 signaling in human breast cancer cells was observed for two of the compounds.

  • 34.
    Sott, R.
    et al.
    University of Gothenburg.
    Granander, J.
    University of Gothenburg.
    Dinér, P.
    University of Gothenburg.
    Hilmersson, G.
    University of Gothenburg.
    Solution structures of chiral lithium amides with internal sulfide coordination: sulfide versus ether coordination in chiral lithium amides2004In: Tetrahedron-Asymmetry, Vol. 15, no 2, p. 267-274Article in journal (Refereed)
    Abstract [en]

    A series of chiral lithium amides with chelating sulfide groups has been investigated by NMR spectroscopy. These chiral lithium amides have previously been found to mediate higher enantioselectivity in the asymmetric addition of alkyllithium reagents to aldehydes than the corresponding lithium amides containing ether groups. The chiral lithium amido sulfide chelates form homodimers in both diethyl ether and tetrahydrofuran. In diethyl ether both sulfur atoms coordinate to the same lithium while the other lithium in the dimer is solvent coordinated. Tetrahydrofuran favours equivalently solvated homodimers. Mixed dimeric complexes are formed with excess n-butyllithium in both diethyl ether and tetra hydrofuran. The structural information was obtained from observed Li-6,N-15 couplings and cross peaks in the Li-6,H-1 HOESY spectrum. DFT calculations at B3LYP/6-31G(d) level of theory indicate that the Li-S chelate is much less stable than the Li-O chelate. However the calculations indicate that the stability of the dimeric chelates are in agreement with the NMR results of the diethyl ether and tetrahydrofuran solutions. (C) 2003 Elsevier Ltd. All rights reserved.

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