Stereoselective Internal Acyl Migration of 1β-O-Acyl Glucuronides of Enantiomeric 2-Phenylpropionic Acids
スポンサーリンク
概要
- 論文の詳細を見る
Internal acyl migration reactions of 1β-O-acyl glucuronides of 2-arylpropionic acids (profens) are of interest because of their possible role in covalent binding to serum proteins and consequent allergic reactions. The stereoselective degradation of 1β-O-acyl glucuronides of enantiomeric 2-phenylpropionic acids (PAs), the basic structures of profens, in phosphate buffer (pH 7.4) at 37℃, has been investigated using HPLC. Apparent first-order degradation of 1β-O-acyl glucuronide and the sequential appearance of 2-, 3- and 4-O-acyl isomers were observed for each enantiomer. Acyl migration was observed to predominate over hydrolysis as in the other profen glucuronides. All the positional isomers and anomers were characterized using NMR and HPLC-NMR. The overall degradation half-life of (R)- and (S)-PA glucuronides was 1.8 and 3.3 h, respectively. These results suggest that (R)-PA glucuronide could be more susceptible to covalent binding to proteins via acyl migration than the corresponding antipode. The lability of the (R)-diastereomer over the antipode is consistent with previous reports on other profen glucuronides. Thus, the diastereomeric PA glucuronides are considered to be the best model compounds for the computation of structural physicochemical parameters to control the stereoselective internal acyl migration of profen glucuronides because PA has the simplest chemical structure of all the profens.
- 公益社団法人日本薬学会の論文
- 2000-04-01
著者
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長谷川 浩
金沢大学理工研究域物質化学系
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Hashimoto T
Faculty Of Pharmaceutical Sciences Hokuriku University
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橋本 忠
北陸大・薬
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AKIRA Kazuki
School of Pharmacy, Tokyo University of Pharmacy and Life Science
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HASHIMOTO Takao
School of Pharmacy, Tokyo University of Pharmacy and Life Science
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IMACHI Misako
Bruker BioSpin K. K.
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HASEGAWA Hiroshi
School of Environmental Science, University of Shiga Prefecture
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Shinohara Yuki
Faculty Of Pharmaceutical Sciences Mukogawa Women's University
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Shinohara Yoshihiko
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
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Hashimoto T
Hokuriku Univ. Kanazawa Jpn
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Akira K
School Of Pharmacy Tokyo University Of Pharmacy And Life Science
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Akira Kazuki
School Of Pharmacy Tokyo University Of Pharmacy And Life Science
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Imachi M
Bruker Japan Co. Ltd.
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Hashimoto Toshihiro
Fac. Of Pharmaceutical Sciences Tokushima Bunri Univ.
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Shinohara Yoshihiko
School Of Pharmacy Tokyo University Of Pharmacy And Life Science
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Hashimoto Takao
School Of Pharmacy Tokyo University Of Pharmacy And Life Science
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Hasegawa Hiroshi
School Of Environmental Science The University Of Shiga Prefecture
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