Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

Hajime Abe; Hiroki Makida; Masahiko Inouye

doi:10.1016/j.tet.2012.02.069

Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

Hajime Abe^*, Hiroki Makida, Masahiko Inouye

^*Corresponding author for this work

Member of the Board

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

19 Scopus citations

Abstract

Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds.

Original language	English
Pages (from-to)	4353-4361
Number of pages	9
Journal	Tetrahedron
Volume	68
Issue number	23
DOIs	https://doi.org/10.1016/j.tet.2012.02.069
State	Published - 2012/06/10

Keywords

Click chemistry
Convergent synthesis
Foldamers
Helical structure
Huisgen reaction
Pyridylene ethynylene
Saccharide templates

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2012.02.069

Cite this

@article{2e23c70c4e8d49e09a6ed96f08301dfe,

title = "Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction",

abstract = "Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds.",

keywords = "Click chemistry, Convergent synthesis, Foldamers, Helical structure, Huisgen reaction, Pyridylene ethynylene, Saccharide templates",

author = "Hajime Abe and Hiroki Makida and Masahiko Inouye",

year = "2012",

month = jun,

day = "10",

doi = "10.1016/j.tet.2012.02.069",

language = "英語",

volume = "68",

pages = "4353--4361",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "23",

}

TY - JOUR

T1 - Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

AU - Abe, Hajime

AU - Makida, Hiroki

AU - Inouye, Masahiko

PY - 2012/6/10

Y1 - 2012/6/10

N2 - Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds.

AB - Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds.

KW - Click chemistry

KW - Convergent synthesis

KW - Foldamers

KW - Helical structure

KW - Huisgen reaction

KW - Pyridylene ethynylene

KW - Saccharide templates

UR - http://www.scopus.com/inward/record.url?scp=84860656196&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.02.069

DO - 10.1016/j.tet.2012.02.069

M3 - 学術論文

AN - SCOPUS:84860656196

SN - 0040-4020

VL - 68

SP - 4353

EP - 4361

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this