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  • 1.
    Hamnevik, Emil
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Blikstad, Cecilia
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Norrehed, Sara
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Widersten, Mikael
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Kinetic characterization of Rhodococcus ruber DSM 44541 alcohol dehydrogenase A2014Ingår i: Journal of Molecular Catalysis B: Enzymatic, ISSN 1381-1177, E-ISSN 1873-3158, Vol. 99, s. 68-78Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    An increasing interest in biocatalysis and the use of stereoselective alcohol dehydrogenases in synthetic asymmetric catalysis motivates detailed studies of potentially useful enzymes such as alcohol dehydrogenase A (ADH-A) from Rhodococcus ruber. This enzyme is capable of catalyzing enantio-, and regioselective production of phenyl-substituted α-hydroxy ketones (acyloins) which are precursors for the synthesis of a range of biologically active compounds. In this study, we have determined the enzyme activity for a selection of phenyl-substituted vicinal diols and other aryl- or alkyl-substituted alcohols and ketones. In addition, the kinetic mechanism for the oxidation of (R)- and (S)-1-phenylethanol and the reduction of acetophenone has been identified as an Iso Theorell-Chance (hit and run) mechanism with conformational changes of the enzyme-coenzyme binary complexes as rate-determining for the oxidation of (S)-1-phenylethanol and the reduction of acetophenone. The underlying cause of the 270-fold enantiopreference for the (S)-enantiomer of 1-phenylethanol has been attributed to non-productive binding of the R-enantiomer. We have also shown that it is possible to tune the direction of the redox chemistry by adjusting pH with the oxidative reaction being favored at pH values above 7.

  • 2.
    Norrehed, Sara
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Modulation of Molecular Properties: Host–Guest Interactions for Structural Analysis and Chemical Reactions2013Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
    Abstract [en]

    This thesis concerns the construction, use and modulation of various host–guest systems, from small bispidines for binding of inorganic ions to bisporphyrin clips for supramolecular systems.

    Small flexible molecules undergo fast conformational movements when in solution. These conformational movements generate time-averaged population-weighted chemical shifts, coupling constants and NOEs when analysed by NMR spectroscopy. A bisporphyrin clip was designed to be used as a host for restriction of conformational movements of small flexible molecules by ditopic metal-ligand binding. Based on conformational analysis in combination with NMR analysis of molecular flexibility in solution (NAMFIS), the relative stereochemistry of flexible alditol-derived diamines containing three or four consecutive stereocentres could be determined.

    To further explore the idea of conformational deconvolution via host–guest binding, two flexible molecular tweezers with photoswitchable moieties were developed. Upon photoswitching cis/trans isomerisation facilitates the opening and closing of these bisporphyrin hosts. A guest molecule could then be exposed to a “catch and stretch” or “catch and release” effect. Preliminary studies have shown that photoisomerisation of the constructed systems is possible without photodecomposition and preliminary binding studies have been conducted.

    Controlled modulation of molecular conformations is of interest especially if the conformational steering activates a unit working as a nucleator in a larger structure or facilitates a reaction. The protonation-triggered modulation of bispidine conformations has been investigated. In addition to previously reported conformations we have observed that upon diprotonation a bispidine derivative can be driven into the unusual boat-boat conformation.

    Finally, the unexpected formation of persistent organic radicals with a cyclophane motif from the reaction of N,N´-diphenyl-1-5-diazacyclooctane and AgBF4 is described. Interestingly, these diradicals exhibit features such as intramolecular π-stacking without lateral displacement and also intramolecular spin pairing.

     

    Delarbeten
    1. Conformational restriction of flexible molecules in solution by a semirigid bis-porphyrin molecular tweezer
    Öppna denna publikation i ny flik eller fönster >>Conformational restriction of flexible molecules in solution by a semirigid bis-porphyrin molecular tweezer
    Visa övriga...
    2013 (Engelska)Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, nr 34, s. 7131-7138Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    A semirigid bis-porphyrin molecular clip with a glycoluril backbone has been synthesized. The clip provides an adaptable molecular cavity for binding of diamines. Binding constants for diamines of 104–107 M−1 are orders of magnitude higher than those for monoamines of 103 M−1, indicating a preference to bidentate binding. NMR studies confirmed that binding of bidentate guests occurs inside the clip. Short- and medium-size acyclic molecular guests are locked into a single, extended conformation, and also guests with longer flexible chains exhibit considerably less conformational mobility than when free in solution. The size of the cavity adapts to the guest size, as indicated by modelling studies and self diffusion constants of the complexes.

    Nyckelord
    Conformational analysis, NMR spectroscopy, Hosteguest systems, Supramolecular chemistry, Porphyrinoids
    Nationell ämneskategori
    Naturvetenskap Organisk kemi
    Forskningsämne
    Kemi med inriktning mot organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-206036 (URN)10.1016/j.tet.2013.06.013 (DOI)000322098000027 ()
    Forskningsfinansiär
    Vetenskapsrådet
    Tillgänglig från: 2013-08-26 Skapad: 2013-08-26 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
    2. Improved stereochemical analysis of conformationally flexible diamines by binding to a bisporphyrin molecular clip
    Öppna denna publikation i ny flik eller fönster >>Improved stereochemical analysis of conformationally flexible diamines by binding to a bisporphyrin molecular clip
    2013 (Engelska)Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, nr 43, s. 14631-14638Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    The relative stereochemistry of acyclic diamines with several stereogenic centers has been analyzed by NMR spectroscopy in combination with conformational deconvolution. Binding to a bisporphyrin molecular clip improves the stereochemical assignment significantly. The diamines were synthesized from inexpensive sugar alcohols, and their stable hydrochlorides were quantitatively converted into free bases by treatment with ion-exchange resin.

    Nyckelord
    configuration determination, conformational analysis, host–guest systems, N ligands, NMR spectroscopy
    Nationell ämneskategori
    Naturvetenskap Organisk kemi
    Forskningsämne
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-206040 (URN)10.1002/chem.201300533 (DOI)000330288400025 ()
    Forskningsfinansiär
    Vetenskapsrådet
    Tillgänglig från: 2013-08-26 Skapad: 2013-08-26 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
    3. Photomodulable bis-porphyrin molecular tweezers for conformational studies of diamine guests
    Öppna denna publikation i ny flik eller fönster >>Photomodulable bis-porphyrin molecular tweezers for conformational studies of diamine guests
    Visa övriga...
    (Engelska)Manuskript (preprint) (Övrigt vetenskapligt)
    Nationell ämneskategori
    Naturvetenskap
    Identifikatorer
    urn:nbn:se:uu:diva-206039 (URN)
    Tillgänglig från: 2013-08-26 Skapad: 2013-08-26 Senast uppdaterad: 2014-01-23
    4. Protonation-triggered Conformational Modulation of an N,N´‑Dialkylbispidine: First observation of the elusive boat-boat conformer
    Öppna denna publikation i ny flik eller fönster >>Protonation-triggered Conformational Modulation of an N,N´‑Dialkylbispidine: First observation of the elusive boat-boat conformer
    2013 (Engelska)Ingår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, s. 6292-6299Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    Modulation of the solution conformations of N,N′-bis(benzhydryl)bispidine has been achieved by protonation. Conformers have been characterized by NMR spectroscopy using nuclear Overhauser effects and residual dipolar couplings. In contrast to the preference for the chair–chair conformation for the free base and the monoprotonated species, the diprotonated bispidine is revealed to exist as a mixture of chair–boat and boat–boat conformers. While boat–boat conformers of bispidines have previously not been detected, they are here observed to constitute up to 70% of the bispidine population.

    Nationell ämneskategori
    Naturvetenskap Organisk kemi
    Forskningsämne
    Organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-206042 (URN)10.1039/c3ob41122b (DOI)000324507100010 ()
    Forskningsfinansiär
    Vetenskapsrådet
    Tillgänglig från: 2013-08-26 Skapad: 2013-08-26 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
    5. Synthesis of persistent organic dication diradicals incorporating a cyclophane motif with intramolecular pi-stacking
    Öppna denna publikation i ny flik eller fönster >>Synthesis of persistent organic dication diradicals incorporating a cyclophane motif with intramolecular pi-stacking
    Visa övriga...
    (Engelska)Artikel i tidskrift (Övrigt vetenskapligt) Submitted
    Nationell ämneskategori
    Naturvetenskap
    Identifikatorer
    urn:nbn:se:uu:diva-206043 (URN)
    Tillgänglig från: 2013-08-26 Skapad: 2013-08-26 Senast uppdaterad: 2014-01-23Bibliografiskt granskad
  • 3.
    Norrehed, Sara
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Erdélyi, Maté
    Light, Mark E.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Protonation-triggered Conformational Modulation of an N,N´‑Dialkylbispidine: First observation of the elusive boat-boat conformer2013Ingår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 11, s. 6292-6299Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Modulation of the solution conformations of N,N′-bis(benzhydryl)bispidine has been achieved by protonation. Conformers have been characterized by NMR spectroscopy using nuclear Overhauser effects and residual dipolar couplings. In contrast to the preference for the chair–chair conformation for the free base and the monoprotonated species, the diprotonated bispidine is revealed to exist as a mixture of chair–boat and boat–boat conformers. While boat–boat conformers of bispidines have previously not been detected, they are here observed to constitute up to 70% of the bispidine population.

  • 4.
    Norrehed, Sara
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Johansson, Henrik
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Fysikalisk-organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Improved stereochemical analysis of conformationally flexible diamines by binding to a bisporphyrin molecular clip2013Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, nr 43, s. 14631-14638Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The relative stereochemistry of acyclic diamines with several stereogenic centers has been analyzed by NMR spectroscopy in combination with conformational deconvolution. Binding to a bisporphyrin molecular clip improves the stereochemical assignment significantly. The diamines were synthesized from inexpensive sugar alcohols, and their stable hydrochlorides were quantitatively converted into free bases by treatment with ion-exchange resin.

  • 5.
    Norrehed, Sara
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Karlsson, Christoffer
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Nanoteknologi och funktionella material.
    Light, Mark E.
    University of Southampton: Southampton.
    Thapper, Anders
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Molekylär biomimetik.
    Huang, Ping
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Molekylär biomimetik.
    Gogoll, A
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi. Uppsala University.
    Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes2019Ingår i: Monatshefte fuer Chemie, ISSN 0026-9247, E-ISSN 1434-4475, Vol. 150, nr 1, s. 77-84Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    N,N'-Diphenyl-3,7-diazacyclooctane and structurally related N,N'-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C–C coupling reaction to produce dication–diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.

  • 6.
    Norrehed, Sara
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Polavarapu, Prasad
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Yang, Wenzhi
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Fysikalisk-organisk kemi.
    Conformational restriction of flexible molecules in solution by a semirigid bis-porphyrin molecular tweezer2013Ingår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, nr 34, s. 7131-7138Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A semirigid bis-porphyrin molecular clip with a glycoluril backbone has been synthesized. The clip provides an adaptable molecular cavity for binding of diamines. Binding constants for diamines of 104–107 M−1 are orders of magnitude higher than those for monoamines of 103 M−1, indicating a preference to bidentate binding. NMR studies confirmed that binding of bidentate guests occurs inside the clip. Short- and medium-size acyclic molecular guests are locked into a single, extended conformation, and also guests with longer flexible chains exhibit considerably less conformational mobility than when free in solution. The size of the cavity adapts to the guest size, as indicated by modelling studies and self diffusion constants of the complexes.

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