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  • 1
    Electronic Resource
    Electronic Resource
    Solid-state structure and conformation of (Z)-2-(phenylbenzylidene)-3-quinuclidinone, an intermediate in the synthesis of quinuclidine derivatives (1994)
    Springer
    Structural chemistry 5 (1994), S. 183-188 
    Details
    ISSN: 1572-9001
    Keywords: Solid-state structure ; quinuclidine ; X-ray diffraction ; conformation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract (Z)-2-(2-phenylbenzylidene)-3-quinuclidinone, C20H19NO,M r =300.47D crystallizes in the monoclinicP21/c space group witha = 6.9809(2) Å,b=19.0523(2) Å,c = 11.7733(1) Å,β=100.92(2)°,V=1537.5(3) Å3,Z=4,D c = 1.298 g/cm3,D x =1.29 g/cm3 (flotation). Diffractometric data, using CuKα radiation,λ=1.54178 Å, were collected on plate-like crystals. The structure, solved by direct methods was refined to a final R value of 0.037 for the 2645 observed reflections withF o 〉3.0σ(F o ). The molecule shows a trans conformation around the double bond. The quinuclidine and the diphenyl moieties present deformations in their geometric and conformational parameters due to the need of releasing intramolecular strains and/or nonbonded interactions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02262840
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  • 2
    Electronic Resource
    Electronic Resource
    Molecular structures of quinuclidinic neurokinin antagonists: 2-(2-Phenylbenzylidene)-3-(2-X-benzylamino) derivatives (1996)
    Springer
    Structural chemistry 7 (1996), S. 173-181 
    Details
    ISSN: 1572-9001
    Keywords: X-ray structure ; solid-state conformation ; quinuclidine ; neurokinins antagonist
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The solid-state molecular conformations and crystal structures of three analogues of the CP-96,345 molecule, an important nonpeptidic SP antagonist, namely the (±)-2-(3-phenylbenzilidene)-3-(2-benzylamino) quinuclidine, theo-chloro- and theo-methoxy-derivatives, have been determined by X-ray diffusion analyses and refined to finalR values of 0.055, 0.045, and 0.056, respectively. All three molecules in the solid state show the same disposition of the substituents of the double bond and differences in the conformation mainly caused by the need of releasing intramolecular strains and/or nonbonded interactions. The observed molecular structures are compared to the reported solid-state structure of the CP-96,345 and correlated to the biological activity as NK antagonists.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02281228
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  • 3
    Electronic Resource
    Electronic Resource
    Hemoprotein Models Based on a Covalent Helix-Heme-Helix Sandwich: 1. Design, Synthesis, and Characterization (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 340-349 
    Details
    ISSN: 0947-6539
    Keywords: helical structures ; heme proteins ; iron ; peptides ; synthesis design ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In this paper we describe the design, synthesis, and spectroscopic characterization of a covalent helix-heme-helix sandwich named FeIII mimochrome I. It contains deuterohemin bound through both propionyl groups to two identical N-and C-terminal protected nonapeptides as α-helical scaffolds. Each peptide moiety bears a His residue in the central position, which acts as axial ligand to the metal ion. The newly developed synthetic strategy is based on a combination of solution and solid-phase methodologies. It represents a powerful method for obtaining a large variety of analogues containing two symmetric or unsymmetric peptide chains covalently bound to the deuteroporphyrin ring. UV/Visible spectroscopic characterization in buffered 2,2,2-trifluoroethanol/water solution proves low-spin bis(his-tidine) iron(III) coordination; circular dichroism (CD) measurements show an α-helical conformation for the peptide moieties. Thus, all the data are in agreement with the designed hypothetical model regarding both the iron(III) coordination and the peptide chain structural organization.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030305
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  • 4
    Electronic Resource
    Electronic Resource
    Hemoprotein Models Based on a Covalent Helix-Heme-Helix Sandwich: 2. Structural Characterization of CoIII Mimochrome I δ and δ Isomers (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 350-362 
    Details
    ISSN: 0947-6539
    Keywords: cobalt ; helical structures ; heme proteins ; NMR spectroscopy ; por-phyrinoids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: FeIII mimochrome I is the prototype of a new class of hemoprotein models characterized by a covalent helix-heme-helix sandwich. It contains deuterohemin bound through two propionyl groups to two identical N- and C-terminal protected α-helical nonapeptides, each of which bears a His residue (a potential axial lig-and of the iron ion) in the central position. In order to understand better the three-dimensional structure of FeIII mimochrome I and its correlation with spectral properties, we have characterized the fully diamagnetic parent compound CoIII mimochrome I by UV/visible, CD, and NMR spectroscopy, coupled with conformational energy calculations. CoIII mimochrome I is a highly water-soluble compound present in solution as two isomers, which slowly interconvert only at very low pH values. These isomers were isolated and separately characterized. Their UV/visible spectral properties are very similar, while their CD spectral properties differ markedly in both the far UV and Soret regions. The isomers were identified by 1H NMR spectroscopy as diastereomers of the δ and δ type. This is the first example of an accurate three-dimensional structure determination in solution of a hemoprotein mimetic that allows a straightforward correlation between structure and spectral properties.
    Additional Material: 13 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030306
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