Specific complexation of glucose with a diphenylmethane-3,3′- diboronic acid derivative

Correlation between the absolute configuration of mono- and di-saccharides and the circular dichroic activity of the complex

Yutaka Shiomi, Miwako Saisho, Kazuhiko Tsukagoshi, Seiji Shinkai

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111 Citations (Scopus)

Abstract

For the development of receptor molecules that can precisely recognize sugar molecules, we recently synthesized bis-(6-methoxyphenyl)methane-3, 3′-diboronic acid 2. This compound forms 1:1 complexes with mono- and di-saccharides and gives circular dichroism (CD) spectra specific to each saccharide. It was shown on the basis of 1H NMR spectroscopy that the complex with D-glucose is a macrocyclic compound formed by the reaction of the two boronic acids with c/s-1,2-diol and trans-4-OH, 5-CH2OH moieties. Thus, compound 2 becomes CD-active because of asymmetric immobilization of the two chromophoric benzene rings by ring closure with chiral saccharides. The association constants were in the following order: D-glucose (19 000 dm 3 mol-1) ≥ D-talose > D-galactose > D-mannose > D-fructose (= 0 dm3 mol-1) for monosaccharides, and D-maltose (100 dm3 mol-1) > D-cellobiose > D-lactose > D-saccharose (= 0 dm3 mol-1) for disaccharides. In particular, compound 2 showed a very high affinity toward D-glucose. D-Glucose gave a CD spectrum with positive exciton coupling whereas L-glucose gave a CD spectrum with negative exciton coupling. D-Galactose gave a CD spectrum with negative exciton coupling, whereas all other D-mono- and D-disaccharides tested herein gave CD spectra with positive exciton coupling. The results indicate that the absolute configuration of saccharides can be conveniently predicted from the sign and the strength of the CD spectra of their complex with compound 2. This means that the CD spectroscopic method using compound 2 as a receptor probe serves as a new sensory system for sugar molecules.

Original languageEnglish
Pages (from-to)2111-2117
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
Publication statusPublished - Dec 1 1993

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Dichroism
Complexation
Derivatives
Glucose
Acids
Disaccharides
Galactose
Sugars
Molecules
Macrocyclic Compounds
Boronic Acids
Cellobiose
Maltose
Monosaccharides
Methane
Lactose
Mannose
diphenylmethane
Benzene
Fructose

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Specific complexation of glucose with a diphenylmethane-3,3′- diboronic acid derivative: Correlation between the absolute configuration of mono- and di-saccharides and the circular dichroic activity of the complex",
abstract = "For the development of receptor molecules that can precisely recognize sugar molecules, we recently synthesized bis-(6-methoxyphenyl)methane-3, 3′-diboronic acid 2. This compound forms 1:1 complexes with mono- and di-saccharides and gives circular dichroism (CD) spectra specific to each saccharide. It was shown on the basis of 1H NMR spectroscopy that the complex with D-glucose is a macrocyclic compound formed by the reaction of the two boronic acids with c/s-1,2-diol and trans-4-OH, 5-CH2OH moieties. Thus, compound 2 becomes CD-active because of asymmetric immobilization of the two chromophoric benzene rings by ring closure with chiral saccharides. The association constants were in the following order: D-glucose (19 000 dm 3 mol-1) ≥ D-talose > D-galactose > D-mannose > D-fructose (= 0 dm3 mol-1) for monosaccharides, and D-maltose (100 dm3 mol-1) > D-cellobiose > D-lactose > D-saccharose (= 0 dm3 mol-1) for disaccharides. In particular, compound 2 showed a very high affinity toward D-glucose. D-Glucose gave a CD spectrum with positive exciton coupling whereas L-glucose gave a CD spectrum with negative exciton coupling. D-Galactose gave a CD spectrum with negative exciton coupling, whereas all other D-mono- and D-disaccharides tested herein gave CD spectra with positive exciton coupling. The results indicate that the absolute configuration of saccharides can be conveniently predicted from the sign and the strength of the CD spectra of their complex with compound 2. This means that the CD spectroscopic method using compound 2 as a receptor probe serves as a new sensory system for sugar molecules.",
author = "Yutaka Shiomi and Miwako Saisho and Kazuhiko Tsukagoshi and Seiji Shinkai",
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T1 - Specific complexation of glucose with a diphenylmethane-3,3′- diboronic acid derivative

T2 - Correlation between the absolute configuration of mono- and di-saccharides and the circular dichroic activity of the complex

AU - Shiomi, Yutaka

AU - Saisho, Miwako

AU - Tsukagoshi, Kazuhiko

AU - Shinkai, Seiji

PY - 1993/12/1

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N2 - For the development of receptor molecules that can precisely recognize sugar molecules, we recently synthesized bis-(6-methoxyphenyl)methane-3, 3′-diboronic acid 2. This compound forms 1:1 complexes with mono- and di-saccharides and gives circular dichroism (CD) spectra specific to each saccharide. It was shown on the basis of 1H NMR spectroscopy that the complex with D-glucose is a macrocyclic compound formed by the reaction of the two boronic acids with c/s-1,2-diol and trans-4-OH, 5-CH2OH moieties. Thus, compound 2 becomes CD-active because of asymmetric immobilization of the two chromophoric benzene rings by ring closure with chiral saccharides. The association constants were in the following order: D-glucose (19 000 dm 3 mol-1) ≥ D-talose > D-galactose > D-mannose > D-fructose (= 0 dm3 mol-1) for monosaccharides, and D-maltose (100 dm3 mol-1) > D-cellobiose > D-lactose > D-saccharose (= 0 dm3 mol-1) for disaccharides. In particular, compound 2 showed a very high affinity toward D-glucose. D-Glucose gave a CD spectrum with positive exciton coupling whereas L-glucose gave a CD spectrum with negative exciton coupling. D-Galactose gave a CD spectrum with negative exciton coupling, whereas all other D-mono- and D-disaccharides tested herein gave CD spectra with positive exciton coupling. The results indicate that the absolute configuration of saccharides can be conveniently predicted from the sign and the strength of the CD spectra of their complex with compound 2. This means that the CD spectroscopic method using compound 2 as a receptor probe serves as a new sensory system for sugar molecules.

AB - For the development of receptor molecules that can precisely recognize sugar molecules, we recently synthesized bis-(6-methoxyphenyl)methane-3, 3′-diboronic acid 2. This compound forms 1:1 complexes with mono- and di-saccharides and gives circular dichroism (CD) spectra specific to each saccharide. It was shown on the basis of 1H NMR spectroscopy that the complex with D-glucose is a macrocyclic compound formed by the reaction of the two boronic acids with c/s-1,2-diol and trans-4-OH, 5-CH2OH moieties. Thus, compound 2 becomes CD-active because of asymmetric immobilization of the two chromophoric benzene rings by ring closure with chiral saccharides. The association constants were in the following order: D-glucose (19 000 dm 3 mol-1) ≥ D-talose > D-galactose > D-mannose > D-fructose (= 0 dm3 mol-1) for monosaccharides, and D-maltose (100 dm3 mol-1) > D-cellobiose > D-lactose > D-saccharose (= 0 dm3 mol-1) for disaccharides. In particular, compound 2 showed a very high affinity toward D-glucose. D-Glucose gave a CD spectrum with positive exciton coupling whereas L-glucose gave a CD spectrum with negative exciton coupling. D-Galactose gave a CD spectrum with negative exciton coupling, whereas all other D-mono- and D-disaccharides tested herein gave CD spectra with positive exciton coupling. The results indicate that the absolute configuration of saccharides can be conveniently predicted from the sign and the strength of the CD spectra of their complex with compound 2. This means that the CD spectroscopic method using compound 2 as a receptor probe serves as a new sensory system for sugar molecules.

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