Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore

Kahee Fujita; Tadashi Ueda; Taiji Imoto; Iwao Tabushi; Namiko Toh; Toshitaka Koga

doi:10.1016/0045-2068(82)90049-9

Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore

Kahee Fujita, Tadashi Ueda, Taiji Imoto, Iwao Tabushi, Namiko Toh, Toshitaka Koga

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

44 Citations (Scopus)

Abstract

A capped cyclodextrin, 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin, was prepared in order to detect any conformational change of the host upon the guest binding. The association constant between the cyclodextrin and 1-adamantanecarboxylate, cyclohexanecarboxylate, p-methylbenzoate, 3,3-dimethylbutyrate, or 2,2-dimethylpropionate was enhanced 20, 5.3, 3.7, 2.3, or 2.0 times, respectively, by chromophore capping. The changes in the electronic, NMR, and circular dichroism spectra as well as pK_a of this cyclodextrin upon binding of the guest strongly indicate a conformational change around the chromophoric moiety of the cyclodextrin.

Original language	English
Pages (from-to)	72-84
Number of pages	13
Journal	Bioorganic Chemistry
Volume	11
Issue number	1
DOIs	https://doi.org/10.1016/0045-2068(82)90049-9
Publication status	Published - Mar 1982
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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10.1016/0045-2068(82)90049-9

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title = "Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore",

abstract = "A capped cyclodextrin, 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin, was prepared in order to detect any conformational change of the host upon the guest binding. The association constant between the cyclodextrin and 1-adamantanecarboxylate, cyclohexanecarboxylate, p-methylbenzoate, 3,3-dimethylbutyrate, or 2,2-dimethylpropionate was enhanced 20, 5.3, 3.7, 2.3, or 2.0 times, respectively, by chromophore capping. The changes in the electronic, NMR, and circular dichroism spectra as well as pKa of this cyclodextrin upon binding of the guest strongly indicate a conformational change around the chromophoric moiety of the cyclodextrin.",

author = "Kahee Fujita and Tadashi Ueda and Taiji Imoto and Iwao Tabushi and Namiko Toh and Toshitaka Koga",

year = "1982",

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T1 - Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore

AU - Fujita, Kahee

AU - Ueda, Tadashi

AU - Imoto, Taiji

AU - Tabushi, Iwao

AU - Toh, Namiko

AU - Koga, Toshitaka

PY - 1982/3

Y1 - 1982/3

N2 - A capped cyclodextrin, 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin, was prepared in order to detect any conformational change of the host upon the guest binding. The association constant between the cyclodextrin and 1-adamantanecarboxylate, cyclohexanecarboxylate, p-methylbenzoate, 3,3-dimethylbutyrate, or 2,2-dimethylpropionate was enhanced 20, 5.3, 3.7, 2.3, or 2.0 times, respectively, by chromophore capping. The changes in the electronic, NMR, and circular dichroism spectra as well as pKa of this cyclodextrin upon binding of the guest strongly indicate a conformational change around the chromophoric moiety of the cyclodextrin.

AB - A capped cyclodextrin, 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin, was prepared in order to detect any conformational change of the host upon the guest binding. The association constant between the cyclodextrin and 1-adamantanecarboxylate, cyclohexanecarboxylate, p-methylbenzoate, 3,3-dimethylbutyrate, or 2,2-dimethylpropionate was enhanced 20, 5.3, 3.7, 2.3, or 2.0 times, respectively, by chromophore capping. The changes in the electronic, NMR, and circular dichroism spectra as well as pKa of this cyclodextrin upon binding of the guest strongly indicate a conformational change around the chromophoric moiety of the cyclodextrin.

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Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore

Abstract

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