Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media

Minoru Waki; Hajime Abe; Masahiko Inouye

doi:10.1002/chem.200600315

Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media

Minoru Waki, Hajime Abe^*, Masahiko Inouye

^*Corresponding author for this work

Member of the Board

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

88 Scopus citations

Abstract

Water-soluble poly(m-ethynylpyridine)s were designed to realize saccharide recognition in protic media. UV/Vis, ¹HNMR, and fluorescence measurements revealed that the polymer forms a helical higher order structure by solvophobic interactions between the ethynylpyridine units in the protic medium. The resulting pore in the helix behaves like a binding pocket in proteins, by taking advantage of inwardly directed hydrogen-bonding functional groups of the polymers. Molecular recognition of native saccharides by the polymers was investigated by circular dichroism (CD). The chirality of the saccharide was transferred to the helical sense of the polymers, accompanied by the appearance of induced CDs (ICDs) in the absorptive region of the polymers. In MeOH/water (10/1), mannose and allose showed intense ICDs, and the apparent association constant between the polymer and D-mannose was 14M ^-1.

Original language	English
Pages (from-to)	7839-7847
Number of pages	9
Journal	Chemistry - A European Journal
Volume	12
Issue number	30
DOIs	https://doi.org/10.1002/chem.200600315
State	Published - 2006/10/16

Keywords

Helical structures
Hydrogen bonds
Molecular recognition
Pi interactions
Supramolecular chemistry

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.200600315

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title = "Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media",

abstract = "Water-soluble poly(m-ethynylpyridine)s were designed to realize saccharide recognition in protic media. UV/Vis, 1HNMR, and fluorescence measurements revealed that the polymer forms a helical higher order structure by solvophobic interactions between the ethynylpyridine units in the protic medium. The resulting pore in the helix behaves like a binding pocket in proteins, by taking advantage of inwardly directed hydrogen-bonding functional groups of the polymers. Molecular recognition of native saccharides by the polymers was investigated by circular dichroism (CD). The chirality of the saccharide was transferred to the helical sense of the polymers, accompanied by the appearance of induced CDs (ICDs) in the absorptive region of the polymers. In MeOH/water (10/1), mannose and allose showed intense ICDs, and the apparent association constant between the polymer and D-mannose was 14M -1.",

keywords = "Helical structures, Hydrogen bonds, Molecular recognition, Pi interactions, Supramolecular chemistry",

author = "Minoru Waki and Hajime Abe and Masahiko Inouye",

year = "2006",

month = oct,

day = "16",

doi = "10.1002/chem.200600315",

language = "英語",

volume = "12",

pages = "7839--7847",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "30",

}

TY - JOUR

T1 - Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media

AU - Waki, Minoru

AU - Abe, Hajime

AU - Inouye, Masahiko

PY - 2006/10/16

Y1 - 2006/10/16

N2 - Water-soluble poly(m-ethynylpyridine)s were designed to realize saccharide recognition in protic media. UV/Vis, 1HNMR, and fluorescence measurements revealed that the polymer forms a helical higher order structure by solvophobic interactions between the ethynylpyridine units in the protic medium. The resulting pore in the helix behaves like a binding pocket in proteins, by taking advantage of inwardly directed hydrogen-bonding functional groups of the polymers. Molecular recognition of native saccharides by the polymers was investigated by circular dichroism (CD). The chirality of the saccharide was transferred to the helical sense of the polymers, accompanied by the appearance of induced CDs (ICDs) in the absorptive region of the polymers. In MeOH/water (10/1), mannose and allose showed intense ICDs, and the apparent association constant between the polymer and D-mannose was 14M -1.

AB - Water-soluble poly(m-ethynylpyridine)s were designed to realize saccharide recognition in protic media. UV/Vis, 1HNMR, and fluorescence measurements revealed that the polymer forms a helical higher order structure by solvophobic interactions between the ethynylpyridine units in the protic medium. The resulting pore in the helix behaves like a binding pocket in proteins, by taking advantage of inwardly directed hydrogen-bonding functional groups of the polymers. Molecular recognition of native saccharides by the polymers was investigated by circular dichroism (CD). The chirality of the saccharide was transferred to the helical sense of the polymers, accompanied by the appearance of induced CDs (ICDs) in the absorptive region of the polymers. In MeOH/water (10/1), mannose and allose showed intense ICDs, and the apparent association constant between the polymer and D-mannose was 14M -1.

KW - Helical structures

KW - Hydrogen bonds

KW - Molecular recognition

KW - Pi interactions

KW - Supramolecular chemistry

UR - http://www.scopus.com/inward/record.url?scp=33750315369&partnerID=8YFLogxK

U2 - 10.1002/chem.200600315

DO - 10.1002/chem.200600315

M3 - 学術論文

C2 - 16847986

AN - SCOPUS:33750315369

SN - 0947-6539

VL - 12

SP - 7839

EP - 7847

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 30

ER -

Helix formation in synthetic polymers by hydrogen bonding with native saccharides in protic media

Abstract

Keywords

ASJC Scopus subject areas

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