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 journalArticle

43 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 pKa of this cyclodextrin upon binding of the guest strongly indicate a conformational change around the chromophoric moiety of the cyclodextrin.

Original languageEnglish
Pages (from-to)72-84
Number of pages13
JournalBioorganic Chemistry
Volume11
Issue number1
DOIs
Publication statusPublished - Mar 1982

Fingerprint

Cyclodextrins
Chromophores
Circular Dichroism
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore. / Fujita, Kahee; Ueda, Tadashi; Imoto, Taiji; Tabushi, Iwao; Toh, Namiko; Koga, Toshitaka.

In: Bioorganic Chemistry, Vol. 11, No. 1, 03.1982, p. 72-84.

Research output: Contribution to journalArticle

Fujita, Kahee ; Ueda, Tadashi ; Imoto, Taiji ; Tabushi, Iwao ; Toh, Namiko ; Koga, Toshitaka. / Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore. In: Bioorganic Chemistry. 1982 ; Vol. 11, No. 1. pp. 72-84.
@article{1a5e51505f614de2af8053a48f0c02a2,
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",
month = "3",
doi = "10.1016/0045-2068(82)90049-9",
language = "English",
volume = "11",
pages = "72--84",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Academic Press Inc.",
number = "1",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0001888909&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001888909&partnerID=8YFLogxK

U2 - 10.1016/0045-2068(82)90049-9

DO - 10.1016/0045-2068(82)90049-9

M3 - Article

AN - SCOPUS:0001888909

VL - 11

SP - 72

EP - 84

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

IS - 1

ER -