Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer

Yuki Ohishi; Hajime Abe; Masahiko Inouye

doi:10.1002/ejoc.201701522

Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer

Yuki Ohishi, Hajime Abe^*, Masahiko Inouye

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

An amphiphilic pyridine–phenol alternating oligomer, in which oligo(ethylene glycol) chains are attached at the 4-positions of the pyridine and the phenol rings, was synthesized as a helical host to realize saccharide recognition in water. This oligomer was soluble not only in less-polar solvents but also in water at room temperature. Circular dichroism investigations revealed that the oligomer could recognize several kinds of saccharides and their derivatives, including glycodrugs to form chiral higher-order structures in water. Especially, the oligomer showed high affinity for d-glucosamine, and their association constants were over 10³ m^–1.

Original language	English
Pages (from-to)	6975-6979
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	46
DOIs	https://doi.org/10.1002/ejoc.201701522
State	Published - 2017/12/15

Keywords

Helical structures
Host–guest systems
Hydrogen bonds
Molecular recognition
Supramolecular chemistry

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201701522

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title = "Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer",

abstract = "An amphiphilic pyridine–phenol alternating oligomer, in which oligo(ethylene glycol) chains are attached at the 4-positions of the pyridine and the phenol rings, was synthesized as a helical host to realize saccharide recognition in water. This oligomer was soluble not only in less-polar solvents but also in water at room temperature. Circular dichroism investigations revealed that the oligomer could recognize several kinds of saccharides and their derivatives, including glycodrugs to form chiral higher-order structures in water. Especially, the oligomer showed high affinity for d-glucosamine, and their association constants were over 103 m–1.",

keywords = "Helical structures, Host–guest systems, Hydrogen bonds, Molecular recognition, Supramolecular chemistry",

author = "Yuki Ohishi and Hajime Abe and Masahiko Inouye",

note = "Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

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T1 - Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer

AU - Ohishi, Yuki

AU - Abe, Hajime

AU - Inouye, Masahiko

PY - 2017/12/15

Y1 - 2017/12/15

N2 - An amphiphilic pyridine–phenol alternating oligomer, in which oligo(ethylene glycol) chains are attached at the 4-positions of the pyridine and the phenol rings, was synthesized as a helical host to realize saccharide recognition in water. This oligomer was soluble not only in less-polar solvents but also in water at room temperature. Circular dichroism investigations revealed that the oligomer could recognize several kinds of saccharides and their derivatives, including glycodrugs to form chiral higher-order structures in water. Especially, the oligomer showed high affinity for d-glucosamine, and their association constants were over 103 m–1.

AB - An amphiphilic pyridine–phenol alternating oligomer, in which oligo(ethylene glycol) chains are attached at the 4-positions of the pyridine and the phenol rings, was synthesized as a helical host to realize saccharide recognition in water. This oligomer was soluble not only in less-polar solvents but also in water at room temperature. Circular dichroism investigations revealed that the oligomer could recognize several kinds of saccharides and their derivatives, including glycodrugs to form chiral higher-order structures in water. Especially, the oligomer showed high affinity for d-glucosamine, and their association constants were over 103 m–1.

KW - Helical structures

KW - Host–guest systems

KW - Hydrogen bonds

KW - Molecular recognition

KW - Supramolecular chemistry

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U2 - 10.1002/ejoc.201701522

DO - 10.1002/ejoc.201701522

M3 - 学術論文

AN - SCOPUS:85038113212

SN - 1434-193X

VL - 2017

SP - 6975

EP - 6979

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 46

ER -

Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer

Abstract

Keywords

ASJC Scopus subject areas

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