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  • Publication
    Métadonnées seulement
    3-D-Glucopyranosyl-6-methoxy-2-benzoxazolinone (MBOA-N-Glc) is an insect detoxification product of maize 1,4-benzoxazin-3-ones
    (2014) ; ; ;
    Köhler, Angela
    ;
    Wouters, Felipe C.
    ;
    Vassão, Daniel G.
    ;
    Gershenzon, Jonathan
    ;
    Wolfender, Jean-Luc
    ;
    ; ;
    Glauser, Gaetan
    In order to defend themselves against arthropod herbivores, maize plants produce 1,4-benzoxazin-3-ones (BXs), which are stored as weakly active glucosides in the vacuole. Upon tissue disruption, BXs come into contact with ?-glucosidases, resulting in the release of active aglycones and their breakdown products. While some aglycones can be reglucosylated by specialist herbivores, little is known about how they detoxify BX breakdown products. Here we report on the structure of an N-glucoside, 3-?-d-glucopyranosyl-6-methoxy-2-benzoxazolinone (MBOA-N-Glc), purified from Spodoptera frugiperda faeces. In vitro assays showed that MBOA-N-Glc is formed enzymatically in the insect gut using the BX breakdown product 6-methoxy-2-benzoxazolinone (MBOA) as precursor. While Spodoptera littoralis and S. frugiperda caterpillars readily glucosylated MBOA, larvae of the European corn borer Ostrinia nubilalis were hardly able to process the molecule. Accordingly, Spodoptera caterpillar growth was unaffected by the presence of MBOA, while O. nubilalis growth was reduced. We conclude that glucosylation of MBOA is an important detoxification mechanism that helps insects tolerate maize BXs.
  • Publication
    Métadonnées seulement
    An Efficient Photoinduced Deprotection of Aromatic Acetals and Ketals
    A novel type of photodeprotection reaction of simple arom. acetals and ketals is described. The deprotection is highly efficient under optimized conditions. The arom. ring confers the photoreactivity to the compds. The efficiency of the process depends on the structure of the acetal moiety. The common minor side reaction, the photooxidn., becomes the major reaction pathway in the case of cyclic acetals. The use of photon as only reagent makes this procedure esp. attractive for acetal deprotection. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Click chemistry applied in the synthesis of symmetrical triphenylene-based discotic liquid-crystalline dimers
    Sym. triphenylene dimers connected by a bis-triazole moiety have been synthesized and characterized. The bis-triazole part is formed as final step utilizing a straightforward double click reaction (CuAAC) allowing further structural variations of the linker. The 1,3-bis(triazol-1-yl)propyltriphenylene-based dimer display columnar mesophase over a wide range of temps. starting at ambient temp. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    1,4-Bis(hex-yloxy)-2,5-diiodo-benzene
    (2010) ; ;
    Sereda, Olha
    ;
    Neels, Antonia
    ;
    The centrosymmetric title compound, C(18)H(28)I(2)O(2), crystallized in the monoclinic space group P2(1)/c with the alkyl chains having extended all-trans conformations, similar to those in the centrosymmetric bromo analogue [Li et al. (2008 (black right triangle)). Acta Cryst. E64, o1930] that crystallized in the triclinic space group P. The difference between the two structures lies in the orientation of the two alkyl chains with respect to the C(aromatic)-O bond. In the title compound, the O-C(alk-yl)-C(alk-yl)-C(alk-yl) torsion angle is 55.8 (5)°, while in the bromo analogue this angle is -179.1 (2)°. In the title compound, the C-atoms of the alkyl chain are almost coplanar [maximum deviation of 0.052 (5) Å] and this mean plane is inclined to the benzene ring by 50.3 (3)°. In the bromo-analogue, these two mean planes are almost coplanar, making a dihedral angle of 4.1 (2)°. Another difference between the crystal structures of the two compounds is that in the title compound there are no halide(midline ellipsis)halide inter-actions. Instead, symmetry-related mol-ecules are linked via C-H(midline ellipsis)? contacts, forming a two-dimensional network.
  • Publication
    Métadonnées seulement
    2-(2-Naphthyl)-1,3-dioxane
    The title compd., C14H14O2, crystallizes in the chiral monoclinic space group P21. Crystallog. data and at. coordinates are given. This acetal is composed of a planar naphthalene ring with a 1,3-dioxane ring substituent, which has a chair conformation. In the crystal structure, symmetry-related mols. are connected via a weak C-H...O interaction to form a helical chain propagating in [010]. While there are no ?-? stacking interactions present, there are weak C-H...? interactions involving the naphthalene arom. rings, which link the helical chains to form a two-dimensional network in the (011) plane. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    1,4-Bis(hexyloxy)-2,5-diiodobenzene
    (2010) ; ;
    Sereda, Olha
    ;
    Neels, Antonia
    ;
    The centrosym. title compd., C18H28I2O2, crystd. in the monoclinic space group P21/c with the alkyl chains having extended all-trans conformations, similar to those in the centrosym. bromo analog that crystd. in the triclinic space group P?1. The difference between the 2 structures lies in the orientation of the 2 alkyl chains with respect to the C(arom.)-O bond. In the title compd., the O-Calkyl-Calkyl-Calkyl torsion angle is 55.8(5)°, while in the bromo analog this angle is -179.1(2)°. In the title compd., the C-atoms of the alkyl chain are almost coplanar [max. deviation of 0.052(5) Å] and this mean plane is inclined to the benzene ring by 50.3(3)°. In the bromo-analog, these 2 mean planes are almost coplanar, making a dihedral angle of 4.1(2)°. Another difference between the crystal structures of the 2 compds. is that in the title compd. there are no halide...halide interactions. Instead, symmetry-related mols. are linked via C-H...? contacts, forming a 2D network. Crystal data: monoclinic, P21/n, a = 9.441(9), b = 7.8455(6), c = 13.457(2) Å, ? = 92.148(12)°, Z = 2, 1216 obsd. reflections with I > 2(I), 101 refined parameters, R[F2 > 2?(F2)] = 0.029, wR(F2) = 0.055. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    1,4-Bis[4-(tert-butyldiphenylsilyl)buta-1,3-diynyl]benzene
    The title centrosym. mol., C46H42Si2, is composed of a central benzene ring with buta-1,3-diynyl chains at positions 1 and 4. These chains are terminated by tert-butyldiphenylsilyl groups, hence the mol. is dumbbell in shape. The mols. are connected via C-H...? interactions in the structure, so forming an undulating 2D network in the bc plane. There is also a weak ?-? interaction involving centrosym. related Ph rings with a centroid-centroid distance of 3.8359(11) Å. Crystal data: monoclinic, P21/c, a = 8.535(1), b = 17.2060(14), c = 13.4923(14) Å, ? = 104.064(9)°, Z = 2, 3260 obsd. reflections with I > 2(I), 220 refined parameters, R[F2 > 2?(F2)] = 0.044, wR(F2) = 0.104. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    2-(2-Naphth-yl)-1,3-dioxane
    The title compound, C(14)H(14)O(2), crystallizes in the chiral monoclinic space group P2(1). This acetal is composed of a planar naphthalene ring with a 1,3-dioxane ring substituent, which has a chair conformation. In the crystal structure, symmetry-related mol-ecules are connected via a weak C-H(midline ellipsis)O inter-action to form a helical chain propagating in [010]. While there are no ?-? stacking inter-actions present, there are weak C-H(midline ellipsis)? inter-actions involving the naphthalene aromatic rings, which link the helical chains to form a two-dimensional network in the (011) plane.
  • Publication
    Métadonnées seulement
    1,4-Bis[4-(tert-butyl-diphenyl-silyl)buta-1,3-diyn-yl]benzene
    The title centrosymmetric mol-ecule, C(46)H(42)Si(2), is composed of a central benzene ring with buta-1,3-diynyl chains at positions 1 and 4. These chains are terminated by tert-butyl-diphenyl-silyl groups, hence the molecule is dumbbell in shape. The mol-ecules are connected via C-H(midline ellipsis)? inter-actions in the structure, so forming an undulating two-dimensional network in the bc plane. There is also a weak ?-? inter-action involving centrosymmetrically related phenyl rings with a centroid-centroid distance of 3.8359 (11) Å.
  • Publication
    Accès libre
    2-(2-Naphthyl)-1,3-dioxane
    The title compound, C14H14O2, crystallizes in the chiral monoclinic space group P21. This acetal is composed of a planar naphthalene ring with a 1,3-dioxane ring substituent, which has a chair conformation. In the crystal structure, symmetry-related molecules are connected via a weak C-H ··· O interaction to form a helical chain propagating in [010]. While there are no - stacking interactions present, there are weak C-H ··· π interactions involving the naphthalene aromatic rings, which link the helical chains to form a two-dimensional network in the (011) plane.