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PubMed1997

Inclusion of Volatile Organic Compounds into Natural Cyclodextrins and Their Branched Cyclodextrins in the Gaseous Phase

The adsorption isotherms of water, the differential heat of adsorption, and the entropy of adsorbed water were investigated to elucidate the structure of stability of cyclodextrins (CyD) and branched CyD's. The amount adsorbed on branched CyD's increased with increasing relative humidity. The steep rise in the amount adsorbed at higher relative humidities indicated that the structure of branched CyD's was affected by the water molecules at these higher relative humidities. The bonding force between alpha-CyD's and water molecules was stronger than that between their branched CyD's and water, while that between beta-CyD's and water was weaker than that between their branched CyD's and water. We have used activated carbons for the recovery of organic solvents. There are polar groups on the activated carbon surface. Therefore, the recovered organic solvents were degraded by these groups. However, such polar groups are not expected for the hydroxyl groups of the CyD's. The amounts of 1,1,1-trichloroethane, benzene, and toluene included in natural CyD's and their branched CyD's were measured. The amounts of organic solvents included in the CyD's depended upon the cavity radii and the glucosyl and maltosyl functional groups of the CyD's and the radii of the organic solvent molecules.

Journal Article↗
PubMed2006

Biphasic aqueous organometallic catalysis promoted by cyclodextrins: can surface tension measurements explain the efficiency of chemically modified cyclodextrins?

Methylated and hydroxypropylated cyclodextrins (CDs) are highly efficient mass transfer promoters in biphasic aqueous organometallic processes. The surface tension measurements demonstrated that these CDs adsorb at air-water interface and allowed to determine surface excess of CD by using Gibbs adsorption equation. Interestingly, a good correlation between surface excess and catalytic activity was obtained in the case of hydroformylation and Tsuji-Trost reactions. These results point out the importance of CD adsorption at the interface in biphasic aqueous organometallic processes.

Journal Article↗
PubMed2001

Cyclodextrin-modified biosensors: comparision of cyclodextrin-linked ferrocenes as mediators in sol-gel and screen-printed formats for sensing acetylcholine.

This work reports the comparison of a sol-gel and a screen-printed biosensor format using new mediators and a sensitive thin-film (ref. 1: P. Kataky and D. Parker, Analyst, 1996, 121, 1829) to enhance the sensitivity and stability of biosensors. The new mediators were per-alkylated cyclodextrin linked ferrocenes and a control, ferrocene aminocarboxylic acid. The thin film comprised a cocktail with polyurethane, plasticiser, lipophilic anion and a perethylated beta-CD. The analyte targeted was acetylcholine using the established horseradish peroxidase-choline-oxidase-acetylcholine esterase relay. The screen-printed electrode format showed a marked decrease in oxidation potential, the magnitude of the shift depended on the structure of the mediator and the membrane covering. Although lower oxidation-potentials were observed with the sol-gel format sensors, their response was more akin to aqueous solution behaviour. Electrocatalytic currents were observed suggesting a highly efficient electron transfer process.

Journal Article↗
PubMed1976

Studies on cyclodextrin glycosyltransferase. IV. Enzymatic synthesis of 3-O-alpha-D-glucopyranosyl-L-sorbose and 4-O-alpha-D-glucopyranosyl-D-xylose using cyclodextrin glycosyltransferase.

The acceptor specificity of the transglycosylation reaction of cyclodextrin glycosyltransferase[EC 2.4.1.19] was investigated using various sugars and sugar alcohols. L-Sorbose, D-xylose, and D-galactose, which contain configurational or structural changes relative to the D-glucopyranose unit at positions other than position 1, were also shown to be efficient acceptors in the transglycosylation reaction of this enzyme. It was shown by chemical and enzymatic methods that this enzyme could transfer glycosyl residues only to the C3-hydroxyl group of L-sorbose and C4-hydroxyl group of D-xylose, producing oligosaccharides terminated by 3-O-alpha-D-glucopyranosyl-L-sorbose and 4-O-alpha-D-glucopyranosyl-D-xylose at the reducing ends, respectively.

Acetates↗
PubMed2001

A new mixed acetal-type substitution pattern for alpha-cyclodextrin. Preparation of hexakis (3-O-benzyl)- alpha-cyclodextrin.

alpha-CD was converted into hexakis[2,6-di-O-(methoxydimethyl)methyl]-alpha-CD by a proton-catalyzed reaction with 2-methoxypropene. Subsequent benzylation under Brimacombe conditions resulted in the fully protected compound, from which the acid-sensitive acetal groups were removed to obtain hexakis(3-O-benzyl)-alpha-cyclodextrin. The structure of all of the compounds synthesized was confirmed by 13C J-ECHO, COSY, HETCOR and HMBC NMR measurements.

Journal Article↗
PubMed2005

Preparation of alpha-cyclodextrin-terminated polyrotaxane consisting of beta-cyclodextrins and pluronic as a building block of a biodegradable network.

A beta-CD-based biodegradable polyrotaxane was prepared by capping both terminals of polypseudorotaxane consisting of hydrazide-terminated PEG-block-PPG-block-PEG (Pluronic P-105) and beta-CD-succinates with mono-aldehyde alpha-CDs. By decreasing pH, the fluorescent intensity of TNS was increased with time, indicating cleavage of the terminal hydrazone bonds followed by beta-CD-succinate release. The terminal alpha-CD moieties of the polyrotaxane are useful for self-assembled formation with some guest molecules. [Diagram: see text]

Biodegradation, Environmental↗
PubMed2000

Crystal structure of octakis(2,3,6-tri-O-methyl)-gamma-cyclodextrin x 4.5 H2O: evidence for conformational flexibility of permethylated cyclodextrins.

Octakis(2,3,6-tri-O-methyl)-gamma-CD (TRIMEG) cocrystallized at 18 degrees C with 4.5 water molecules in the orthorhombic space group P2(1)2(1)2(1), unit cell dimensions a = 10.7879(3), b = 29.0580(9), c = 32.2909(11) A. The TRIMEG macrocycle is in a 'round' form with all glucose units oriented syn, and one O-6-CH3 methoxy group points 'toward' the molecular cavity. The TRIMEG x 4.5 H2O molecules are stacked to form infinite cylinders with the central cavities aligned into channels filled for each TRIMEG by 4.5 water molecules distributed over 15 partially occupied sites. This structure differs from the two known structures of TRIMEG in which two diametrically opposed glucoses are oriented anti to yield an 'elliptical' form, and their O-6-CH3 groups are directed 'toward' the cavity and close it at this side to form a bowl-shaped molecule.

Carbohydrate Conformation↗
PubMed2000

Synthesis of novel heterobranched beta-cyclodextrins from alpha-D-mannosylmaltotriose and beta-cyclodextrin by the reverse action of pullulanase, and isolation and characterization of the products.

Alpha-D-mannosyl-maltotriose (Man-G3) were synthesized from methyl alpha-mannoside and maltotriose by the transfer action of alpha-mannosidase. (Man-G3)-betaCD and (Man-G3)2-betaCD were produced in about 20% and 4% yield, respectively when Aerobacter aerogenes pullulanase (160 units per 1 g of Man-G3) was incubated with the mixture of 1.6 M Man-G3 and 0.16 M betaCD at 50 degrees C for 4 days. The reaction products, (Man-G3)-betaCD were separated to three peaks by HPLC analysis on a YMC-PACK A-323-3 column and (Man-G3)2-betaCD were separated to several peaks by HPLC analysis on a Daisopak ODS column. The major product of (Man-G3)-betaCDs was identified as 6-O-alpha-(6(3)-O-alpha-D-mannosylmaltotriosyl)-betaCD by FAB-MS and NMR spectroscopies. The structures of (Man-G3)2-betaCDs were analyzed by TOF-MS and NMR spectroscopies, and confirmed by comparison of elution profiles of their hydrolyzates by alpha-mannosidase and glucoamylase on a graphitized carbon column with those of the authentic di-glucosyl-betaCDs. The structures of three main components of (Man-G3)2-betaCDs were identified as 6(1),6(2)-, 6(1),6(3)- and 6(1),64-di-O-(63-O-alpha-D-mannosyl-maltotriosyl)-betaCD.

Cyclodextrins↗
PubMed2005

Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors.

In this study, enantioseparations of five phenothiazines, including promethazine, ethopropazine, trimeprazine, methotrimeprazine, and thioridazine, in CD-modified CZE using dual CD systems consisting of randomly sulfate-substituted CD (MI-S-beta-CD) and a neutral CD as chiral selectors in a citrate buffer (100 mM) at pH 3.0 were investigated. The results indicate that MI-S-beta-CD is an excellent chiral selector for enantioseparation of ethopropazine. The enantiomers of promethazine can also be baseline-resolved with MI-S-beta-CD at concentrations in the range of 0.5-1.0% w/v. On the other hand, thioridazine and trimeprazine interact strongly with neutral CDs. As a result, the enantioselectivity of these two phenothiazines is remarkably and synergistically enhanced with increasing the concentration of neutral CDs in the presence of MI-S-beta-CD and simultaneous enantioseparations of these phenothiazines, except for methotrimeprazine, could favorably be achieved with the use of dual CD systems. Moreover, by varying the concentration of beta-CD or gamma-CD at a fixed concentration of MI-S-beta-CD (0.75% w/v) reversal of the enantiomer migration order of promethazine occurred. This may be attributable to the opposite effects of charged and neutral CDs on the mobility of the enantiomers of promethazine.

Cyclodextrins↗