Hydrolysis of β-Glucosyl Ester Linkage of p-Hydroxybenzoyl β-D-Glucose, a Chemically Synthesized Glucoside, by β-Glucosidases

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概要

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• To investigate the hydrolysis of glucosyl esters by β-glucosidase, p-hydroxybenzoyl β-D-glucose(pHBG) was chemically synthesized. The hydrolytic activity of some β-glucosidases for pHBG was compared to that for p-nitrophenyl β-glucoside(pNPG). The Clavibacter michiganense and Flavobacterium johnsonae enzymes could hydrolyze pHBG and steviol glycosides which are natural glucosyl esters. The commercial β-glucosidase originating from Caldocellum saccharolyticum also hydrolyzes pHBG despite having no activity for steviol glycosides. The β-glucosidase from Aspergillus niger cleaved the glucosyl ester linkage much more weakly than the glucosidic linkage. The pH-activity profile for the hydrolysis of pHBG was similar to that of pNPG by the C.saccharolyticum β-glucosidase. The similar profiles for these substrates suggested that the active site for the glucosyl ester chemically resembles that for glucoside with respect to catalysis. Kinetic analysis of the C.saccharolyticum β-glucosidase for mixed substrates of pHBG and pNPG showed that the hydrolysis of pHBG competed with that of pNPG. This result indicated that there is only one active site for both the glucosyl ester and glucoside. Mass spectroscopic analysis of the hydrolysates of pHBG in H_2^<18>O suggested that β-glucosidase hydrolyzes glucosyl esters between the anomeric carbon of glucose and the carbonyl oxygen, not between the carbonyl carbon and the carbonyl oxygen.

• 社団法人日本生物工学会の論文
• 2000-12-25

著者

• KITAHATA Sumio

  Osaka Municipal Technical Research Institute

• KISO TARO

  Osaka Municipal Technical Research Institute

• MIYOSHI Shinsuke

  Showa Sangyo Co., Ltd.

• NAKANO HIROFUMI

  Osaka Municipal Technical Research Institute, and Yashiro Co, Ltd.,

• Kitahata S

  Department Of Bioscience And Biotecnology Shinshu University

• OKAMOTO KATSUYUKI

  Showa Sangyo Co. Ltd.

• Kiso Taro

  Department Of Biochemistry Osaka Municipal Technical Research Institute

• Kobayashi S

  Fukui Univ. Technol. Fukui Jpn

• Nakano H

  Department Of Biochemistry Osaka Municipal Technical Research Institute

• Nakano H

  Kyoto Prefectural Univ. Kyoto Jpn

• Okamoto K

  Showa Sangyo Co. Ltd.

• Nakano Hirofumi

  Osaka Municipal Technical Research Institute

• Miyoshi Shinsuke

  Showa Sangyo Co. Ltd.

• Miyoshi Shinsuke

  Showa Sangyo Co.ltd.

• Nakano Hirofumi

  Department Of Chemistry Faculty Of Science Osaka University

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