- Synthesis of cyclodextrins with carboxylic acids at the secondary rim and an evaluation of their properties as chemzymes for glycoside hydrolysis
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Seven β-cyclodextrin-mono-, -di-or -tetra-O-acetic acids were prepared and investigated for their propertiesas catalysts of the hydrolysis of four nitrophenyl glycosides.
- Zhou, You,Lindbaeck, Emil,Marinescu, Lavinia G.,Pedersen, Christian Marcus,Bols, Mikael
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- Photo-responsive host-guest complexation directs dynamic covalent condensation of phenyl boronic acid andd-fructose
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Inspired by the way templates have been used to drive dynamic combinatorial libraries by molecular recognition, we exploited the photo-responsive host-guest interaction of an azo-based photoswitch with permethylated cyclodextrin to reversibly manipulate t
- Klepel, Florian,Ravoo, Bart Jan
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- A facile synthesis of novel cyclodextrin derivatives incorporating one beta-(1,4)-glucosidic bond and their unique inclusion ability.
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Novel cyclodextrin derivatives incorporating one (1,4)-glucosidic bond are easily synthesized in three steps from permethylated alpha- and beta-cyclodextrins, and such host molecules show inclusion selectivity for sodium m-nitrobenzoate over the corresponding p-isomer, in contrast to the cases of the parent permethylated alpha- and beta-cyclodextrins.
- Kida, Toshiyuki,Kikuzawa, Akira,Nakatsuji, Yohji,Akashi, Mitsuru
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- A convenient synthesis of mono-6-hydroxy permethylated β-cyclodextrin via tert-butyldimethylsilylation
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A convenient method to prepare mono-6-hydroxy permethylated β-cyclodextrin (3) via tert-butyldimethylsilylation is described. Mono-6-tert-butyldimethylsilyl-β-cyclodextrin was prepared and treated with NaH and CH3I in the same pot. The protecting group was removed by refluxing with NH4F in CH3OH to give 3 in an overall yield of 43%.
- Chen, Zhen,Bradshaw, Jerald S.,Lee, Milton L.
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- Xylylene Clips for the Topology-Guided Control of the Inclusion and Self-Assembling Properties of Cyclodextrins
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The topology of β-cyclodextrin can be molded, from toroidal to ovoid basket-shaped, by the installation of an o- or m-xylylene moiety connecting two consecutive d-glucopyranosyl units through the secondary O-2(I) and O-3(II) positions. This strategy can be exploited advantageously to precast the cavity for preferential inclusion of globular or planar guests as well as to privilege dimeric or monomeric species in water solution.
- Neva, Tania,Carmona, Thais,Benito, Juan M.,Przybylski, Cédric,Ortiz Mellet, Carmen,Mendicuti, Francisco,García Fernández, José M.
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- A simple synthesis route for selectively methylated β-cyclodextrin using a copper complex sandwich protecting strategy
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This communication reports a novel synthesis route for the preparation of monofunctional-ized β-cyclodextrin in a single stage. The approach involves only the in-situ protection of secondary hydroxyl groups as an excellent alternative to the classical procedure involving a series of five steps of protection and deprotection of hydroxyl groups (both primary and secondary ones) belonging to β-cyclodextrin.
- Bucur, Stefan,Niculaua, Marius,Ciobanu, Catalina Ionica,Lungu, Neculai Catalin,Mangalagiu, Ionel
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- Enhanced photodynamic therapy through supramolecular photosensitizers with an adamantyl-functionalized porphyrin and a cyclodextrin dimer
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A supramolecular photosensitizer was constructed using a tetra-adamantane-functionalized porphyrin and a dimer of permethyl-β-cyclodextrin through host-guest interaction and self-assembly. The porphyrin/cyclodextrin alternating structure of supramolecular
- Xia, Lei,Wu, Jian,Huang, Baoxuan,Gao, Yun,Tian, Jia,Zhang, Weian
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supporting information
p. 11134 - 11137
(2020/10/05)
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- Cyclodextrin-based ionic liquids as enantioselective stationary phases in gas chromatography
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New permethylated mono-6-deoxy-6-pyridin-1-ium and mono-6-deoxy-6-(1-vinyl- 1H-imidazol-3-ium)-α- and -β-cyclodextrin trifluoromethanesulfonate ionic liquids were synthesized from the corresponding permethylated mono-6-hydroxycyclodextrins in a one-pot reaction and solvent-free procedure. Regioselective transformation of native α- and β-cyclodextrins with the use of a bulky tert-butyldiphenylsilyl protecting group afforded the desired 6-monosubstituted permethylated cyclodextrin derivatives in moderate yields. The new ionic liquids were tested as stationary phases in capillary GC columns towards chiral discrimination in enantio-GC analysis of racemic mixtures. The permethylated 6-deoxy-6-pyridin-1-ium-α-cyclodextrin trifluoromethanesulfonate displayed good enantiomeric separations for some racemic esters and lactones, as well as epoxides. In particular, for both the racemic whiskey lactone and the high boiling point menthyl laurate, not successfully separated in a commercial cyclodextrin phase, the enantiomeric separations were achieved isothermally at 140 °C. In phase: Permethylated mono-6-hydroxy-α- and -β-cyclodextrins react with pyridine or 1-vinylimidazole in the presence of triflic anhydride in a solvent-free procedure to yield new roomerature ionic liquids (ILs). These ILs have been used as stationary phases in gas chromatography; enantiomeric separations are achieved (see figure for whiskey lactone) with permethylated mono-6-deoxy-6-(pyridin-1-ium)-α-cyclodextrin trifluoromethanesulfonate. Copyright
- Costa, Nuno,Matos, Sara,Da Silva, Marco D. R. Gomes,Pereira, M. Manuela A.
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p. 1466 - 1474
(2014/01/06)
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- Enantiomeric discrimination in solid-state cyclodextrin complexes
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Cyclodextrins were used to prepare inclusion complexes of a volatile chiral compound, 1,7-dioxaspiroundecane 1, a pheromone of Dacus oleae.The included pheromone was recovered from the inclusion complexes.Cyclodextrins that were unsymmetrically substituted with at least one unit different from the others could form inclusion complexes preferentially with the S enantiomer of the pheromone. cyclodextrin / heptakis(2,6-di-O-methyl)-β-cyclodextrin / heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin / pheromone / inclusion complex / 1,7-dioxaspiroundecane
- Bahaddi, Youssef,Galons, Herve,Rysanek, Nicole
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p. 330 - 332
(2007/10/02)
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- Conformational Analyses of Alkylated β-Cyclodextrins by NMR Spectroscopy
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β-Cyclodextrin was derivatized with 1-bromoalkanes of different chain lengths.The yield as well as the purity of the resulting cyclodextrin derivatives were improved by using solvent mixtures instead of pure solvents.The heptakis(2,6-di-O-alkyl)- and hept
- Meier-Augenstein, Wolfram,Burger, Barend V.,Spies, Hendrik S. C.,Burger, Wina J. G.
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p. 877 - 886
(2007/10/02)
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- Molecular Mass Determination of Some Organic Compounds in the Range of 1500
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Osmometric molecular mass determinations of neutral medium-polar model compounds in the range of 1000 - 1500 could be carried out with an error of less then 8 percent.Electron impact (EI) mass spectrometry failed.The fast atom bombardment (FAB) method pro
- Kemper, Bernd,Musso, Hans,Smith, Richard J.,,Williams, Dudley H.
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p. 310 - 313
(2007/10/02)
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- Improvement of dissolution and suppository release characteristics of flurbiprofen by inclusion complexation with heptakis(2,6-di-O-methyl)-β-cyclodextrin
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The inclusion behavior of methylated β-cyclodextrins, heptakis(2,6-di-O-methyl)-β-cyclodextrin (2), and heptakis-(2,3,6-tri-O-methyl)-β-cyclodextrin (3) in solution and the solid state was compared with that of natural β-cyclodextrin (1) using an anti-inflammatory drug, flurbiprofen, as a guest molecule. Stability constants were determined by the solubility method at various temperatures, and the thermodynamic parameters were calculated for inclusion complex formation in aqueous solution. The solid complexes were obtained in a molar ratio of 1:1, and their dissolution behavior and release from suppository bases were examined. The data suggest that the inclusion mode of the complex with 3 is somewhat different from that of the complexes with 1 and 2. From a practical point of view, 2 seems to be particularly useful for improving the pharmaceutical properties of flurbiprofen in various dosage forms.
- Uekama,Imai,Maeda,Irie,Hirayama,Otagiri
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p. 841 - 845
(2007/10/02)
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