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Thevenet, Damien
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Thevenet, Damien
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Voici les éléments 1 - 10 sur 11
- PublicationMétadonnées seulement3-D-Glucopyranosyl-6-methoxy-2-benzoxazolinone (MBOA-N-Glc) is an insect detoxification product of maize 1,4-benzoxazin-3-ones(2014)
; ; ; ; ; Glauser, GaetanIn 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. - PublicationMétadonnées seulementAn Efficient Photoinduced Deprotection of Aromatic Acetals and Ketals(2011)
; 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)] - PublicationMétadonnées seulementClick chemistry applied in the synthesis of symmetrical triphenylene-based discotic liquid-crystalline dimers(2011)
; 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)] - PublicationMétadonnées seulement1,4-Bis(hex-yloxy)-2,5-diiodo-benzene(2010)
; ; - PublicationMétadonnées seulement2-(2-Naphthyl)-1,3-dioxane(2010)
; ; 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)] - PublicationMétadonnées seulement1,4-Bis(hexyloxy)-2,5-diiodobenzene(2010)
; ; - PublicationMétadonnées seulement1,4-Bis[4-(tert-butyldiphenylsilyl)buta-1,3-diynyl]benzene(2010)
; ; 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)] - PublicationMétadonnées seulement2-(2-Naphth-yl)-1,3-dioxane(2010)
; ; 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. - PublicationMétadonnées seulement1,4-Bis[4-(tert-butyl-diphenyl-silyl)buta-1,3-diyn-yl]benzene(2010)
; ; 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. - PublicationAccès libre2-(2-Naphthyl)-1,3-dioxane(2010)
; ; 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.