D3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module

Hajime Abe; Asuka Horii; Shinya Matsumoto; Motoo Shiro; Masahiko Inouye

doi:10.1021/ol800783a

D_3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module

Hajime Abe^*, Asuka Horii, Shinya Matsumoto, Motoo Shiro, Masahiko Inouye

^*Corresponding author for this work

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14 Scopus citations

Abstract

(Chemical Equation Presented) A D_3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in ¹H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl₃, and was studied by ¹H NMR and X-ray analysis.

Original language	English
Pages (from-to)	2685-2688
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/ol800783a
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol800783a

Cite this

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title = "D3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module",

abstract = "(Chemical Equation Presented) A D3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in 1H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl3, and was studied by 1H NMR and X-ray analysis.",

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T1 - D3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module

AU - Abe, Hajime

AU - Horii, Asuka

AU - Matsumoto, Shinya

AU - Shiro, Motoo

AU - Inouye, Masahiko

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) A D3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in 1H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl3, and was studied by 1H NMR and X-ray analysis.

AB - (Chemical Equation Presented) A D3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in 1H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl3, and was studied by 1H NMR and X-ray analysis.

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SN - 1523-7060

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JO - Organic Letters

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