Selective recognition of alkanoates by a β-cyclodextrin flexibly capped with a chromophore

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The association between 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin 1 and sodium n-alkanoate, sodium 2,2-dimethylpropionate, or sodium 3,3-dimethylbutyrate was investigated. Host-guest association was measured by means of electronic spectroscopy and circular dichroism spectroscopy and ascertained to be 1:1. The inclusion of 2,2-dimethylpropionate or butanoate marginally affected the circular dichroism spectrum of 1. The inclusion of 3,3-dimethylbutyrate, hexanoate, octanoate, decanoate, or dodecanoate, however, dramatically affected the spectrum of 1. The plots of molecular ellipticities of the inclusion complexes against the carbon number of the n-alkanoates were sigmoid. From these observations, the effective size of the guest molecule to push the chromophore in the cavity to the capping position was estimated. From the similarity of the spectrum of the octanoate-1 complex to that of 1-adamantanecarboxylate-1 complex, the carbon chain of octanoate appears to be folded in the cavity of the cyclodextrin.

Original languageEnglish
Pages (from-to)108-114
Number of pages7
JournalBioorganic Chemistry
Volume11
Issue number2
DOIs
Publication statusPublished - Jan 1 1982

Fingerprint

Cyclodextrins
Chromophores
Sodium
Circular Dichroism
Spectrum Analysis
Carbon
Laurates
Decanoates
Circular dichroism spectroscopy
Sigmoid Colon
Spectroscopy
Molecules
octanoic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Selective recognition of alkanoates by a β-cyclodextrin flexibly capped with a chromophore. / Fujita, Kahee; Ueda, Tadashi; Imoto, Taiji; Tabushi, Iwao; Toh, Namiko; Koga, Toshitaka.

In: Bioorganic Chemistry, Vol. 11, No. 2, 01.01.1982, p. 108-114.

Research output: Contribution to journalArticle

Fujita, Kahee ; Ueda, Tadashi ; Imoto, Taiji ; Tabushi, Iwao ; Toh, Namiko ; Koga, Toshitaka. / Selective recognition of alkanoates by a β-cyclodextrin flexibly capped with a chromophore. In: Bioorganic Chemistry. 1982 ; Vol. 11, No. 2. pp. 108-114.
@article{5a77de738d29473cbf1c3bce786e2d1f,
title = "Selective recognition of alkanoates by a β-cyclodextrin flexibly capped with a chromophore",
abstract = "The association between 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin 1 and sodium n-alkanoate, sodium 2,2-dimethylpropionate, or sodium 3,3-dimethylbutyrate was investigated. Host-guest association was measured by means of electronic spectroscopy and circular dichroism spectroscopy and ascertained to be 1:1. The inclusion of 2,2-dimethylpropionate or butanoate marginally affected the circular dichroism spectrum of 1. The inclusion of 3,3-dimethylbutyrate, hexanoate, octanoate, decanoate, or dodecanoate, however, dramatically affected the spectrum of 1. The plots of molecular ellipticities of the inclusion complexes against the carbon number of the n-alkanoates were sigmoid. From these observations, the effective size of the guest molecule to push the chromophore in the cavity to the capping position was estimated. From the similarity of the spectrum of the octanoate-1 complex to that of 1-adamantanecarboxylate-1 complex, the carbon chain of octanoate appears to be folded in the cavity of the cyclodextrin.",
author = "Kahee Fujita and Tadashi Ueda and Taiji Imoto and Iwao Tabushi and Namiko Toh and Toshitaka Koga",
year = "1982",
month = "1",
day = "1",
doi = "10.1016/0045-2068(82)90023-2",
language = "English",
volume = "11",
pages = "108--114",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Academic Press Inc.",
number = "2",

}

TY - JOUR

T1 - Selective recognition of alkanoates by a β-cyclodextrin flexibly capped with a chromophore

AU - Fujita, Kahee

AU - Ueda, Tadashi

AU - Imoto, Taiji

AU - Tabushi, Iwao

AU - Toh, Namiko

AU - Koga, Toshitaka

PY - 1982/1/1

Y1 - 1982/1/1

N2 - The association between 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin 1 and sodium n-alkanoate, sodium 2,2-dimethylpropionate, or sodium 3,3-dimethylbutyrate was investigated. Host-guest association was measured by means of electronic spectroscopy and circular dichroism spectroscopy and ascertained to be 1:1. The inclusion of 2,2-dimethylpropionate or butanoate marginally affected the circular dichroism spectrum of 1. The inclusion of 3,3-dimethylbutyrate, hexanoate, octanoate, decanoate, or dodecanoate, however, dramatically affected the spectrum of 1. The plots of molecular ellipticities of the inclusion complexes against the carbon number of the n-alkanoates were sigmoid. From these observations, the effective size of the guest molecule to push the chromophore in the cavity to the capping position was estimated. From the similarity of the spectrum of the octanoate-1 complex to that of 1-adamantanecarboxylate-1 complex, the carbon chain of octanoate appears to be folded in the cavity of the cyclodextrin.

AB - The association between 6-deoxy-6-(p-hydroxy-m-nitrophenacylthio)-β-cyclodextrin 1 and sodium n-alkanoate, sodium 2,2-dimethylpropionate, or sodium 3,3-dimethylbutyrate was investigated. Host-guest association was measured by means of electronic spectroscopy and circular dichroism spectroscopy and ascertained to be 1:1. The inclusion of 2,2-dimethylpropionate or butanoate marginally affected the circular dichroism spectrum of 1. The inclusion of 3,3-dimethylbutyrate, hexanoate, octanoate, decanoate, or dodecanoate, however, dramatically affected the spectrum of 1. The plots of molecular ellipticities of the inclusion complexes against the carbon number of the n-alkanoates were sigmoid. From these observations, the effective size of the guest molecule to push the chromophore in the cavity to the capping position was estimated. From the similarity of the spectrum of the octanoate-1 complex to that of 1-adamantanecarboxylate-1 complex, the carbon chain of octanoate appears to be folded in the cavity of the cyclodextrin.

UR - http://www.scopus.com/inward/record.url?scp=0001007369&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001007369&partnerID=8YFLogxK

U2 - 10.1016/0045-2068(82)90023-2

DO - 10.1016/0045-2068(82)90023-2

M3 - Article

AN - SCOPUS:0001007369

VL - 11

SP - 108

EP - 114

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

IS - 2

ER -