Selective re-binding of saccharide-imprinted [60]fullerene-bisadducts based on a saccharide-boronic acid interaction: Development of a molecular imprinting technique useful in a homogeneous system

Ishi‐i, Tsutomu; Iguchi, Ritsuko; Shinkai, Seiji

doi:10.1016/s0040-4020(99)00117-9

Cited by 26 publications

(20 citation statements)

References 20 publications

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“…The apparent order of diol selectivity for the boronate was cis a,y-diol> cis α,β-diol according to the superior stability of the sugar six-membered boronate ring over five-membered one 12 . Moreover, they pointed out that the carrier abilities of boronic acids was depending of the dative Ν->B bond and of the sugar-boronate complex lipophilicity.…”

Section: Discussionmentioning

confidence: 99%

Γ-Amino-Boronic ACIDS MEDIATED PASSIVE TRANSPORT OF GLYCOPYRANOSIDES THROUGH a LIQUID ORGANIC MEMBRANE

Dıcko¹,

Bui-Van²,

Baboulène³

et al. 2001

Main Group Metal Chemistry

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The ability of γ-amino-propylboronic acids to transport phenyl ß-D-glucopyranoside and phenyl ß-D-galactopyranoside through a liquid organic membrane in the presence of trioctylmethylammonuim chloride was determined. Under the conditions examined, glycoside transport was facilitated by the reversible formation of covalent tetrahedral, anionic glycosideboronate complexes, which partitioned into the organic membrane as lipophilic ion pairs. The apparent order of glycoside selectivity for the tetrahedral boronate transport was to be cis α,γ-diol> α,β-diol. The results indicate that the N->B intramolecular dative bond and the Hydrophile-Lipophile-Balance (HLB) of the formed complex influence the glycoside transport rate.

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Section: Discussionmentioning

confidence: 99%

Γ-Amino-Boronic ACIDS MEDIATED PASSIVE TRANSPORT OF GLYCOPYRANOSIDES THROUGH a LIQUID ORGANIC MEMBRANE

Dıcko¹,

Bui-Van²,

Baboulène³

et al. 2001

Main Group Metal Chemistry

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“…39 The diboronic acid/ [60]fullerene receptors thus obtained showed a good memory for the templated sugars (44-48% d.e.). 40 The results indicate that the molecular imprinting is possible even in the homogeneous solution, utilizing [60]fullerene bearing many reactive C=C double bonds.…”

Section: Combination With the Concept Of Molecular Imprintingmentioning

confidence: 93%

Molecular Design of Synthetic Receptors with Dynamic, Imprinting, and Allosteric Functions

Shinkai¹,

Takeuchi²

2005

Bulletin of the Chemical Society of Japan

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Sugar recognition in an aqueous system has been achieved using a boronic acid–diol interaction. Combination with an intramolecular amino group has enabled us to read out the binding process as a change in the fluorescence intensity. This novel sugar-sensing method has been combined with a concept of “molecular machinery”, providing a new guest-binding mode with allosteric functions. When this method is combined with a concept of “molecular imprinting”, it becomes possible to design sugar-selective receptors created by a combinatorial method. The sugar recognition event is useful as a trigger to control molecular assemblies such as micelles, membranes, vesicles, and gels.

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“…The diboronic acid/[60]fullerene receptors thus obtained showed a good memory for the templated sugars (44-48% d.e. ; Ishi-i et al, 1999b). The results indicate that the molecular imprinting is possible even in the homogeneous solution, utilizing [60]fullerene bearing many reactive C C double bonds.…”

Section: Combination With the Concept Of Molecular Imprintingmentioning

confidence: 94%

Molecular design of synthetic receptors with dynamic, imprinting, and allosteric functions

Shinkai

Takeuchi

2004

Biosensors and Bioelectronics

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Selective re-binding of saccharide-imprinted [60]fullerene-bisadducts based on a saccharide-boronic acid interaction: Development of a molecular imprinting technique useful in a homogeneous system

Cited by 26 publications

References 20 publications

Γ-Amino-Boronic ACIDS MEDIATED PASSIVE TRANSPORT OF GLYCOPYRANOSIDES THROUGH a LIQUID ORGANIC MEMBRANE

Γ-Amino-Boronic ACIDS MEDIATED PASSIVE TRANSPORT OF GLYCOPYRANOSIDES THROUGH a LIQUID ORGANIC MEMBRANE

Molecular Design of Synthetic Receptors with Dynamic, Imprinting, and Allosteric Functions

Molecular design of synthetic receptors with dynamic, imprinting, and allosteric functions

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