ボロン酸による<I>p</I>-ニトロフェニルD-グルコピラノシドの立体特異的加水分解に対するカチオンミセルの顕著な効果

• 大江 猛

  大阪大学大学院工学研究科分子化学専攻

• 木田 敏之

  大阪大学大学院工学研究科分子化学専攻

• 張 万斌

  大阪大学大学院工学研究科分子化学専攻

• 中辻 洋司

  大阪大学大学院工学研究科分子化学専攻

• 池田 功

  大阪大学大学院工学研究科分子化学専攻

書誌事項

タイトル別名

• A Remarkable Effect of Cationic Micelles on Stereospecific Hydrolysis of <I>p</I>-Nitrophenyl D-Glucopyranoside by Boronic Acid

抄録

The hydrolysis rate of p-nitrophenyl α-D-glucopyranoside was greatly enhanced in cationic micelles of hexadecyltrimethylammonium chloride (HTAC) by using phenylboronic acid (PBA) in pH 11.0 phosphate buffer. Stereospecific acceleration of hydrolysis toward the α-anomer over the β-anomer then increased to a high extent. The effect of the type of boronic acid in micelles of HTAC was examined in order to clarify the mechanism of the enhancement of the hydrolysis rate of the α-glucoside and the α/β selectivity in the presence of HTAC by the addition of PBA. The more hydrophobic boronic acid afforded the higher α/β selectivity. p-Decyloxyphenylboronic acid (C₁₀PBA) gave the highest selectivity (k_α/k_β=64) in the presence of cationic micelles. The enhancement of selectivity by the addition of 1mM C₁₀PBA was comparable to that by 7mM methylboronic acid (MBA), which is the highest selectivity obtained in the absence of cationic micelles.

収録刊行物

• 日本油化学会誌

  日本油化学会誌 49 (3), 231-235,276, 2000

  公益社団法人 日本油化学会

キーワード

• selective hydrolysis
• p-nitrophenyl D-glucopyranoside
• boronic acid
• cationic surfactant
• micelle catalyst

詳細情報

• CRID: 1390282679067678592
• NII論文ID: 130001014871
• DOI: 10.5650/jos1996.49.231
• ISSN: 18841996
• ISSN: 13418327
• Web Site: https://www.jstage.jst.go.jp/article/jos1996/49/3/49_3_231/_pdf
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可