Preparation and characterization of 6A-polyamine-mono-substituted β-cyclodextrins

May, Bruce L.; Kean, Suzanna D.; Easton, Christopher J.; Lincoln, Stephen F.

doi:10.1039/a704467d

Cited by 67 publications

(70 citation statements)

References 13 publications

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“…at the wider cyclodextrin rim) appears particularly interesting because it can throw light on the opposite influence that, for the 3-derivatised cyclodextrins, the cavity can exert on their coordination ability [27][28][29][30]. For the 6-functionalised cyclodextrins it was verified that, mainly for steric reasons, the formation constants of metal complexes are lower than those of the corresponding compounds without the cavity [19,20,31,32], and no involvement of the hydroxyls was observed. Both these two aspects may be quite different in the 3-functionalised cyclodextrins.…”

Section: Introductionmentioning

confidence: 92%

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

Cucinotta

Giuffrida

Mendola

et al. 2004

Journal of Chromatography B

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Section: Introductionmentioning

confidence: 92%

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

Cucinotta

Giuffrida

Mendola

et al. 2004

Journal of Chromatography B

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“…Accordingly, it was anticipated that reaction of cinnamaldehyde (8) with 6 A -(2-aminoethylamino)-6 A -deoxy-b-cyclodextrin (15) [81] would give the diazacyclopentane 16. Subsequent cycloaddition followed by hydrolysis would then produce the free cycloadducts 13 and 14 and regenerate the cyclodextrin 15.…”

Section: Resultsmentioning

confidence: 99%

Reversal of Regioselectivity and Enhancement of Rates of Nitrile Oxide Cycloadditions through Transient Attachment of Dipolarophiles to Cyclodextrins

Barr

Lincoln

Easton

2006

Chemistry A European J

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The reactions of nitrile oxides with monosubstituted dipolarophiles, such as propiolamide, typically afford proportionally 80 % or more of the 3,5-disubstituted cycloadducts. By contrast, the reactions of 6(A)-deoxy-6(A)-propynamido-beta-cyclodextrin with 4-tert-butylbenzonitrile oxide and 4-phenylbenzonitrile oxide afford >90 % and approximately 85 % of the corresponding 3,4-disubstituted isoxazoles, respectively. As well as reversing the regioselectivity, the cyclodextrin increases the rates of these cycloadditions. The extent of the acceleration is up to more than three orders of magnitude for the production of the cycloadduct preferred by the cyclodextrin, but even the rate of reaction to give the less favored regioisomer is increased. With 6(A)-deoxy-6(A)-propynamido-beta-cyclodextrin, the cycloadducts are not easily separated from the cyclodextrin, as the amide bond is not readily cleaved. In comparison, the regioselectivity of the cycloadditions of 4-tert-butylbenzonitrile oxide with acrylic acid, methacrylic acid, and crotonic acid is also altered by formation of the corresponding cyclodextrin esters, by factors of 500, >10, and >100, respectively. The rates of cycloaddition are also increased by up to 475 times, and in these cases the products of cycloaddition are readily released from the cyclodextrin through ester hydrolysis. Incorporating these processes into a reaction cycle, acylation of beta-cyclodextrin with p-nitrophenyl acrylate and subsequent treatment first with 4-tert-butylbenzonitrile oxide and then with base, the latter to catalyze ester hydrolysis and regenerate the beta-cyclodextrin, affords proportionally fivefold more of the 3,4-disubstituted isoxazoline than is produced directly from acrylic acid.

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“…The superoxide dismutase (SOD) activities and glutathione peroxidase (GPX) activities were measured with a Shimadzu UV-2401 spectrometer. FT-IR Spectra: Nicolet FT-IR-5DX; in cm [24]. Then, Et 3 N (0.2 ml) was added to the soln.…”

Section: Experimental Partmentioning

confidence: 99%

Synthesis of Organoselenium-Modifiedβ-Cyclodextrins Possessing a 1,2-Benzisoselenazol-3(2H)-one Moiety and Their Enzyme-Mimic Study

Liu

et al. 2002

HCA

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Six novel H 2 O-soluble b-cyclodextrin derivatives containing a 1,2-benzisoselenazol-3(2H)-one moiety were synthesized by a convenient method in 25 ± 60% yield and characterized by MS, elemental analysis, IR, 1 H-NMR, and UV/VIS spectroscopy. The conformations of these b-cyclodextrin derivatives 1 ± 6 were analyzed by circular dichroism and fluorescence-lifetime experiments. The superoxide dismutase (SOD) activities of 1 ± 6 were determined by auto-oxidation of pyrogallol at 25.08 in buffer solution (pH 8.2), giving relatively high SOD activities of up to 121 ± 330 U/mg. Also, the glutathione peroxidase (GPX) activities of hosts 1 ± 6, determined by the method of Wilson at 378 in buffer solution (pH 7.0), show good GPX activities in the range of 0.34 ± 0.86 U/mmol. The mimicking results of the bifunctional artificial enzyme models 1 ± 6 were globally compared with regard to their structural and conformational difference.

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Preparation and characterization of 6A-polyamine-mono-substituted β-cyclodextrins

Cited by 67 publications

References 13 publications

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

3-Amino derivative of β-cyclodextrin: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis

Reversal of Regioselectivity and Enhancement of Rates of Nitrile Oxide Cycloadditions through Transient Attachment of Dipolarophiles to Cyclodextrins

Synthesis of Organoselenium-Modifiedβ-Cyclodextrins Possessing a 1,2-Benzisoselenazol-3(2H)-one Moiety and Their Enzyme-Mimic Study

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