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 language | English |
|---|---|
| Pages (from-to) | 72-84 |
| Number of pages | 13 |
| Journal | Bioorganic Chemistry |
| Volume | 11 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Mar 1982 |
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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 journal › Article
}
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.
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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 -