Cooperative binding by aggregated mono-6-(alkylamino)-.beta.-cyclodextrins

Petter, Russell C.; Salek, Jeffrey S.; Sikorski, Christopher T.; Kumaravel, Ganesan; Lin, Fu Tyan

doi:10.1021/ja00166a021

Cited by 469 publications

(280 citation statements)

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“…Mono[6-O-(p-toluenesulfonyl)]-β-CD was prepared from β-CD and ptoluenesulfonyl chloride in aqueous alkaline solution. 12 The phosphate buffer (0.10 mol·dm…”

Section: Methodsmentioning

confidence: 99%

Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

2008

Bulletin of the Korean Chemical Society

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A novel anthraquinone diamino-bridged bis(β-cyclodextrin) 2 was synthesized. The inclusion complexation behaviors of the native β-cyclodextrin 1 and the novel bis(β-cyclodextrin) 2 with guests, such as acridine red (AR), neutral red (NR), ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-(p-toluidinyl) naphthalenesulfonate (TNS) and rhodamine B (RhB) were investigation by fluorescence, circular dichroism and 2D NMR spectroscopy. The spectral titrations were performed in phosphate buffer (pH 7.20) showed the highest binding constant towards ANS up to 34.8 times higher than that of 1. The 2D NMR spectra of bis(β-cyclodextrin) 2 with RhB and TNS were performed to confirm the binding mode. The increased binding affinity and molecular selectivity of guests by bis(β-cyclodextrin) 2 were discussed from the viewpoint of the size/shape-fit concept and multipoint recognition mechanism.

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“…Mono[6-O-(p-toluenesulfonyl)]-β-CD was prepared from β-CD and ptoluenesulfonyl chloride in aqueous alkaline solution. 12 The phosphate buffer (0.10 mol·dm…”

Section: Methodsmentioning

confidence: 99%

Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

2008

Bulletin of the Korean Chemical Society

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“…Normally, the pK a s of amino groups are well 48. 17 The lower values for these amino groups located on the rim of the CyD cavity on 3b should be attributable to the effect of the many proximal hydroxyl groups and/or the hydrophobic cavity itself. …”

Section: A-amino-3a-deoxy-(2as3as)-cyclodextrins K Takahashi Et Almentioning

confidence: 99%

Characterization and structural determination of 3A-amino-3A-deoxy-(2AS, 3AS)-cyclodextrins by NMR spectroscopy

Takahashi

Andou

Fujiwara

2012

Polym J

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The proton and carbon nuclear magnetic resonance (NMR) resonances have been assigned for 3A-amino-3A-deoxy-(2AS,3AS)-a-, b-and c-cyclodextrins (CyDs) (3a, 3b and 3c). In these CyDs, a glucose residue has been replaced by an altro-pyranose unit with an axial hydroxyl group. Assignments were made with one-dimensional NMR and COSY, TOCSY, ROESY and CHSHF (heteronuclear shift correlation) spectra. Titration by NMR shift changes gave amino-group pK a values of 7.73 and 8.84 for 3b and 6A-amino-6A-deoxy-b-CyD (6b), respectively. Polymer Journal ( Keywords: altro-cyclodextrin; hydrogen bonding; NMR; structural assignment; titration INTRODUCTIONCarbohydrates are key recognition elements in biological processes. However, in most cases, the role of carbohydrates and the detailed mechanisms of these events are still poorly understood. It seems that a clear model of the structure of carbohydrates is very important for understanding the role of carbohydrates in these processes. Carbohydrates look much simpler than other biomolecules as they differ from each other mainly by stereochemistry. However, carbohydrates actually have much more information capacity than proteins because they vary by linkages and stereochemistry and can be branched. The structure determination of complex oligosaccharides involves discovering the primary structure, stereochemistry, sequence, linkages and anomeric configurations; thus, it is actually a very challenging problem.Cyclodextrins (CyDs) are naturally occurring cyclic carbohydrates consisting of 6-8 glucopyranosyl residues linked by a-1,4 glycosidic bonds. They have a hydrophobic cavity and form inclusion complexes with various guest molecules in aqueous solution and solid state.

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“…Firstly, Mono-6-OTs-β-CD was synthesized according to the method reported in the literature [38]. In a typical experiment, β-CD (30.0 g, 26.4 mmol) was suspended in 250 mL of water, and 10 mL NaOH aqueous solution (8.2 mol·L -1 ) was added dropwise over 1 h. When the suspension became homogeneous slightly yellow solution, 15 mL of p-TsCl acetonitrile solution (13.2 mol·L -1 ) was added dropwise over 2 h. This process resulted in the formation of a white precipitate.…”

Section: Preparation Of Mono-6-(hexanediamino)-β-cy-clodextrin (Hda-βmentioning

confidence: 99%

<i>β</i>-cyclodextrin Covalently Functionalized Single-Walled Carbon Nanotubes: Synthesis, Characterization and a Sensitive Biosensor Platform

Gao¹,

Cao²,

Song³

et al. 2011

JBNB

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In this study, we presented the preparation of β-cyclodextrin (β-CD) covalently functionalized single-walled carbon nanotubes (SWCNTs) and its application in modifying the solid glass carbon electrode (GCE). Cyclic voltammetry (CV) method was employed to evaluate the performance of the modified GCE. Solubility experiment indicated the conjugation of SWCNTs and β-CD, SWCNTs-β-CD with 8 wt% β-CD content could be well dispersed in water. High-resolution transmission electron microscopy (HRTEM) demonstrated that the aggregated SWCNTs bundle were effectively exfoliated to small bundle, even individual tube. The β-CD component was grafted on the side walls as well as tips of SWCNTs, and the grafted β-CD component was not uniformly coated on the surface of SWCNTs. The CV measurements indicated the performance of the GCE modified by SWCNTs-β-CD was better than that of the GCE modified by the hybrid of SWCNTs

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Cooperative binding by aggregated mono-6-(alkylamino)-.beta.-cyclodextrins

Cited by 469 publications

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Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

Characterization and structural determination of 3A-amino-3A-deoxy-(2AS, 3AS)-cyclodextrins by NMR spectroscopy

<i>β</i>-cyclodextrin Covalently Functionalized Single-Walled Carbon Nanotubes: Synthesis, Characterization and a Sensitive Biosensor Platform

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Cooperative binding by aggregated mono-6-(alkylamino)-.beta.-cyclodextrins

Cited by 469 publications

References 0 publications

Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules

Characterization and structural determination of 3A-amino-3A-deoxy-(2AS, 3AS)-cyclodextrins by NMR spectroscopy

&lt;i&gt;β&lt;/i&gt;-cyclodextrin Covalently Functionalized Single-Walled Carbon Nanotubes: Synthesis, Characterization and a Sensitive Biosensor Platform

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<i>β</i>-cyclodextrin Covalently Functionalized Single-Walled Carbon Nanotubes: Synthesis, Characterization and a Sensitive Biosensor Platform