Stabilization of chiral helices for saccharide-linked ethynylpyridine oligomers possessing a conformationally well-defined linkage

Fumihiro Kayamori; Hajime Abe; Masahiko Inouye

doi:10.1002/ejoc.201201376

Stabilization of chiral helices for saccharide-linked ethynylpyridine oligomers possessing a conformationally well-defined linkage

Fumihiro Kayamori, Hajime Abe^*, Masahiko Inouye

^*Corresponding author for this work

Member of the Board

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

17 Scopus citations

Abstract

Tetrameric and octameric 2,6-pyridylene ethynylene oligomers linked to a β-D-glucopyranoside template through an o-phenylene linker were prepared and studied for their higher-order structure. These oligomers formed chiral helical structures through intramolecular hydrogen bonding between the ethynylpyridine moiety and the glucoside template. The rigidity of the o-phenylene linker stabilizes the helical structure to improve its CD activity and resistance against protic surroundings. Furthermore, the helical stabilization was enhanced by the addition of Cu(OTf)₂ and Zn(NO ₃)₂ salts. Tetrameric and octameric 2,6-pyridylene ethynylene oligomers joined to a β-D-glucopyranoside by a o-phenylene linker were prepared and their higher-order structure studied. The chiral helical structures formed by intramolecular H-bonding and linker stabilization improve CD activity and resistance to protic surroundings. Stabilization was enhanced with the addition of Cu(OTf)₂ and Zn(NO₃) ₂ salts.

Original language	English
Pages (from-to)	1677-1682
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.201201376
State	Published - 2013/03

Keywords

Circular dichroism
Helical structures
Hydrogen bonds
Nitrogen heterocycles
Salt effect

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201201376

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title = "Stabilization of chiral helices for saccharide-linked ethynylpyridine oligomers possessing a conformationally well-defined linkage",

abstract = "Tetrameric and octameric 2,6-pyridylene ethynylene oligomers linked to a β-D-glucopyranoside template through an o-phenylene linker were prepared and studied for their higher-order structure. These oligomers formed chiral helical structures through intramolecular hydrogen bonding between the ethynylpyridine moiety and the glucoside template. The rigidity of the o-phenylene linker stabilizes the helical structure to improve its CD activity and resistance against protic surroundings. Furthermore, the helical stabilization was enhanced by the addition of Cu(OTf)2 and Zn(NO 3)2 salts. Tetrameric and octameric 2,6-pyridylene ethynylene oligomers joined to a β-D-glucopyranoside by a o-phenylene linker were prepared and their higher-order structure studied. The chiral helical structures formed by intramolecular H-bonding and linker stabilization improve CD activity and resistance to protic surroundings. Stabilization was enhanced with the addition of Cu(OTf)2 and Zn(NO3) 2 salts.",

keywords = "Circular dichroism, Helical structures, Hydrogen bonds, Nitrogen heterocycles, Salt effect",

author = "Fumihiro Kayamori and Hajime Abe and Masahiko Inouye",

year = "2013",

month = mar,

doi = "10.1002/ejoc.201201376",

language = "英語",

pages = "1677--1682",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "9",

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T1 - Stabilization of chiral helices for saccharide-linked ethynylpyridine oligomers possessing a conformationally well-defined linkage

AU - Kayamori, Fumihiro

AU - Abe, Hajime

AU - Inouye, Masahiko

PY - 2013/3

Y1 - 2013/3

N2 - Tetrameric and octameric 2,6-pyridylene ethynylene oligomers linked to a β-D-glucopyranoside template through an o-phenylene linker were prepared and studied for their higher-order structure. These oligomers formed chiral helical structures through intramolecular hydrogen bonding between the ethynylpyridine moiety and the glucoside template. The rigidity of the o-phenylene linker stabilizes the helical structure to improve its CD activity and resistance against protic surroundings. Furthermore, the helical stabilization was enhanced by the addition of Cu(OTf)2 and Zn(NO 3)2 salts. Tetrameric and octameric 2,6-pyridylene ethynylene oligomers joined to a β-D-glucopyranoside by a o-phenylene linker were prepared and their higher-order structure studied. The chiral helical structures formed by intramolecular H-bonding and linker stabilization improve CD activity and resistance to protic surroundings. Stabilization was enhanced with the addition of Cu(OTf)2 and Zn(NO3) 2 salts.

AB - Tetrameric and octameric 2,6-pyridylene ethynylene oligomers linked to a β-D-glucopyranoside template through an o-phenylene linker were prepared and studied for their higher-order structure. These oligomers formed chiral helical structures through intramolecular hydrogen bonding between the ethynylpyridine moiety and the glucoside template. The rigidity of the o-phenylene linker stabilizes the helical structure to improve its CD activity and resistance against protic surroundings. Furthermore, the helical stabilization was enhanced by the addition of Cu(OTf)2 and Zn(NO 3)2 salts. Tetrameric and octameric 2,6-pyridylene ethynylene oligomers joined to a β-D-glucopyranoside by a o-phenylene linker were prepared and their higher-order structure studied. The chiral helical structures formed by intramolecular H-bonding and linker stabilization improve CD activity and resistance to protic surroundings. Stabilization was enhanced with the addition of Cu(OTf)2 and Zn(NO3) 2 salts.

KW - Circular dichroism

KW - Helical structures

KW - Hydrogen bonds

KW - Nitrogen heterocycles

KW - Salt effect

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U2 - 10.1002/ejoc.201201376

DO - 10.1002/ejoc.201201376

M3 - 学術論文

AN - SCOPUS:84875023832

SN - 1434-193X

SP - 1677

EP - 1682

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Stabilization of chiral helices for saccharide-linked ethynylpyridine oligomers possessing a conformationally well-defined linkage

Abstract

Keywords

ASJC Scopus subject areas

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