Effect of cyclodextrins and saccharide sensing function of a fluorescent phenylboronic acid in water
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- OZAWA Rimiko
- Department of Chemistry, Faculty of Science and Technology, Sophia University
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- HASHIMOTO Takeshi
- Department of Chemistry, Faculty of Science and Technology, Sophia University
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- YAMAUCHI Akiyo
- Graduate School of Pharmaceutical Science, Tohoku University
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- SUZUKI Iwao
- Graduate School of Pharmaceutical Science, Tohoku University
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- SMITH Bradley D.
- Department of Chemistry and Biochemistry, University of Notre Dame
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- HAYASHITA Takashi
- Department of Chemistry, Faculty of Science and Technology, Sophia University
書誌事項
- タイトル別名
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- Effect of Cyclodextrins on Saccharide Sensing Function of a Fluorescent Phenylboronic Acid in Water
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抄録
An inclusion complex consisting of a fluorescent phenylboronic acid (C1-APB) and β-cyclodextrin (β-CD) acts as a supramolecular saccharide sensor whose response mechanism is based on photoinduced electron transfer (PET). This study evaluated four kinds of cyclodextrins (α-CD, β-CD, γ-CD, and NH2-β-CD) by comparing their pH profiles, and confirmed that β-CD was the best host for C1-APB because the C1-APB/β-CD complex exhibited high affinity for saccharides as well as high fluorescent recovery upon saccharide binding. An investigation of the β-CD concentration effect revealed the formation of a 1:1 inclusion complex of C1-APB with β-CD. The observed saccharide selectivity of the C1-APB/β-CD complex is in the following order: D-fructose (4039 ± 69 M-1) > D-ribose (1083 ± 26 M-1) > L-arabinose (474 ± 11 M-1) > D-galactose (318 ± 3 M-1) > maltotoriose (135 ± 5 M-1) > D-glucose (114 ± 2 M-1) > maltose (81 ± 2 M-1). In addition to monomer emission, dimer emission from pyrene dimers was observed in the spectra for the C1-APB/γ-CD complex, which allowed a ratiometric analysis. This study shows that the combination of a simple fluorescent probe, C1-APB, with various CDs diversifies the response systems for saccharide recognition.
収録刊行物
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- Analytical Sciences
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Analytical Sciences 24 (2), 207-212, 2008
社団法人 日本分析化学会
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詳細情報 詳細情報について
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- CRID
- 1390001204258439936
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- NII論文ID
- 130004441602
- 10021098320
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- NII書誌ID
- AA10500785
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- COI
- 1:CAS:528:DC%2BD1cXit1Ogu74%3D
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- ISSN
- 13482246
- 09106340
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- NDL書誌ID
- 9362792
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- PubMed
- 18270410
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- 抄録ライセンスフラグ
- 使用不可