Selective Binding of Sugar to β‐Cyclodextrin: A Prototype for Sugar–Sugar Interactions in Water

Aoyama, Yasuhiro; Nagai, Y.; Otsuki, Jun-ichi; Kobayashi, Kenji; Toi, Hiroo

doi:10.1002/anie.199207451

Cited by 44 publications

(15 citation statements)

References 17 publications

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“…a 0.2 M phosphate buffer of pH 11.6. 'Earlier workers (17,20,23) obtained values of 2.0, 1.4, and 2.2 mM, using similar methods based on the displacement of the ANS.…”

Section: Discussionmentioning

confidence: 94%

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Dissociation constants of host–guest complexes of alkyl-bearing compounds with β-cyclodextrin and "hydroxypropyl-β-cyclodextrin"

Tee¹,

Gadosy²,

Giorgi³

1996

Can. J. Chem.

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Dissociation constants (Kd) of host-guest complexes formed from P-cyclodextrin or "hydroxypropyl-P-cyclodextrin" (P-CD and Hp-P-CD) and several types of aliphatic guests (alcohols, alkanesulfonate ions, alkylamines, and a-amino acids), with up to eight carbons in a chain, are reported. These constants were determined by inhibition kinetics and by a spectrofluorometric displacement method based on competition with 1-anilino-8-naphthalenesulfonate ion as a fluorescent probe. The value of Kd for a particular amine is close to that for the corresponding alcohol. For linear alkyl derivatives, there are strong correlations between pK, (= -log Kd) and the chain length of the guest, with slopes around 0.5, complementing trends that were noted earlier. Furthermore, the strengths of binding of various aliphatic derivatives to P-CD and to Hp-P-CD are close, with Kd values for the two CDs usually being within a factor of 2 of each other. Overall, for the binding of over 50 alkyl-bearing derivatives, there is a good correlation of pKd for Hp-P-CD with that for P-CD, with unit slope. These observations imply that the binding of simple aliphatic guests to Hp-P-CD is not greatly influenced by the modification of the hydroxyl groups on the primary side of the P-CD cavity but this may not be true for longer aliphatic derivatives (>Cx) or for aromatics that penetrate farther into the CD cavity.

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“…a 0.2 M phosphate buffer of pH 11.6. 'Earlier workers (17,20,23) obtained values of 2.0, 1.4, and 2.2 mM, using similar methods based on the displacement of the ANS.…”

Section: Discussionmentioning

confidence: 94%

“…To determine dissociation constants of amineCD complexes we used competition between the amines and the fluorescent probe ANS for the CD (17)(18)(19)(20)(21)(22)(23). First, dissociation constants (KANS) for the CD.ANS complexes were determined in a basic solution, the same as that to be used with the amines.…”

Section: Methodsmentioning

confidence: 99%

Dissociation constants of host–guest complexes of alkyl-bearing compounds with β-cyclodextrin and "hydroxypropyl-β-cyclodextrin"

Tee¹,

Gadosy²,

Giorgi³

1996

Can. J. Chem.

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“…The figures suggest that 25b in Fig. 1 b Data from [69] c Data from [70] d Data from [71] Table 3 Association constants (K a ) and thermodynamic parameters, determined by microcalorimetry, for binding of monosaccharides to a-cyclodextrin 22a [76] particular might be a promising component for optically responsive carbohydrate-sensing devices. However, the high binding constants are puzzling, given the size mismatch between 25b (*24 Å diameter) and a monosaccharide (*8 Å ), and this system could probably benefit from further study by complementary techniques.…”

Section: Water Soluble Porphyrinsmentioning

confidence: 99%

Progress in biomimetic carbohydrate recognition

Walker

Joshi

Davis

2009

Cell. Mol. Life Sci.

109

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The importance of carbohydrate recognition in biology, and the unusual challenges involved, have lead to great interest in mimicking saccharide-binding proteins such as lectins. In this review, we discuss the design of artificial carbohydrate receptors, focusing on those which work under natural (i.e. aqueous) conditions. The problem is intrinsically difficult because of the similarity between substrate (carbohydrate) and solvent (water) and, accordingly, progress has been slow. However, recent developments suggest that solutions can be found. In particular, the "temple" family of carbohydrate receptors show good affinities and excellent selectivities for certain all-equatorial substrates. One example is selective for O-linked beta-N-acetylglucosamine (GlcNAc, as in the O-GlcNAc protein modification), while another is specific for beta-cellobiosyl and closely related disaccharides. Both show roughly millimolar affinities, matching the strength of some lectin-carbohydrate interactions.

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“…Few systematic investigations into the cyclodextrin binding properties of alicyclic compounds have been made (though some useful results are available [1][2][3][4][5][6][7][8][9][10][11][12] ). In the present paper we augment these relatively few examples of alicyclic guest systems by examining the binding of the three "native" cyclodextrins (R-, -, and γ-cyclodextrin) with some alicyclic carboxylic acids and, for comparison purposes, some phenylalkanoic acids.…”

mentioning

confidence: 99%

Binding of Cyclodextrins to Alicyclic and Aromatic Substrates: Complex Formation of α-, β-, and γ-Cyclodextrins with Substituted Cyclohexanecarboxylic Acids and Phenylalkanoic Acids

Gadre¹,

Rüdiger

Schneider

et al. 1997

Journal of Pharmaceutical Sciences

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0 Complex binding constants of the three native cyclodextrins with seven cyclohexane derivatives (all possessing the carboxylic acid group) and with the series C 6 H 5 (CH 2 ) n COOH (n ) 0 to 4) were measured in aqueous solution at 25°C by potentiometry and the solubility method. These results, combined with literature data, indicate that R-and γ-cyclodextrins bind with comparable strength to both the cyclohexyl and phenyl moieties, with -cyclodextrin binding significantly more strongly. These acid series are compared with several series CH 3 (CH 2 ) n X, where X is CH 3 , COOH, COO -, OH, SO 3 -, etc., and it is concluded that the X group (for X other than methyl) contributes appreciably to complex stability, perhaps by means of an extracavity interaction. The COOH group provides a further augmentation of complex stability. NMR CIS and ROESY results indicate the presence of isomeric complexes in both the cyclohexyl and phenylalkanoic series, and clearly demonstrate the existence of intracavity inclusion. An NOE study of the R-cyclodextrin: cyclohexanecarboxylate system provides evidence for inclusion combined with interaction outside (that is, at the rim of) the cavity.Intense interest in cyclodextrin chemistry in recent years has resulted in the measurement of hundreds of binding constants for complexes comprised of cyclodextrins and aromatic guest molecules. Few systematic investigations into the cyclodextrin binding properties of alicyclic compounds have been made (though some useful results are available 1-12 ). In the present paper we augment these relatively few examples of alicyclic guest systems by examining the binding of the three "native" cyclodextrins (R-, -, and γ-cyclodextrin) with some alicyclic carboxylic acids and, for comparison purposes, some phenylalkanoic acids. These binding studies are supported by nuclear magnetic resonance (NMR) investigations of some of these systems. Experimental SectionMaterialssR-Cyclodextrin, -cyclodextrin, and γ-cyclodextrin (American Maize Products Company) were dried at 95°C for 48 h. Benzoic acid (Aldrich) was recrystallized from water; and phenylalkanoic acids (Aldrich) were recrystallized from water-methanol, their melting points being in good agreement with literature values. 3-Cyclohexenecarboxylic acid (Alfa) and the cyclohexane carboxylic acids (Aldrich) were purified by distillation under reduced pressure. House reverse-osmosis water was further treated with a Sybron/ Barnstead PCS ion-exchange purification system.ApparatussPotentiometric measurements were made with an Orion model 701A pH meter and a Corning semi-micro combination electrode. Spectrophotometric measurements were made with a Hitachi model U-3000 spectrophotometer. The solutions were thermostatted during potentiometric and spectrophotometric measurements at 25°C by means of an external, constant-temperature water bath.NMR experiments were carried out at 500 MHz with a Bruker DRX-500 spectrometer at 303 K with D2O as solvent.ProceduressPotentiometrysThe experimental operation consists of mea...

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Selective Binding of Sugar to β‐Cyclodextrin: A Prototype for Sugar–Sugar Interactions in Water

Cited by 44 publications

References 17 publications

Dissociation constants of host–guest complexes of alkyl-bearing compounds with β-cyclodextrin and "hydroxypropyl-β-cyclodextrin"

Dissociation constants of host–guest complexes of alkyl-bearing compounds with β-cyclodextrin and "hydroxypropyl-β-cyclodextrin"

Progress in biomimetic carbohydrate recognition

Binding of Cyclodextrins to Alicyclic and Aromatic Substrates: Complex Formation of α-, β-, and γ-Cyclodextrins with Substituted Cyclohexanecarboxylic Acids and Phenylalkanoic Acids

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