Syntheses of modified 2-chloro-4-nitrophenyl β-maltopentaosides as useful substrates for assay of human alpha amylase
| Autor: | Shoichi Tokutake, Nobuyuki Yamaji, Kotani Kazuo, Kazunori Saito, Riichiro Uchida |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
chemistry.chemical_classification
biology Stereochemistry Molecular Sequence Data Organic Chemistry Kinetics Oligosaccharides Substrate (chemistry) Glycoside General Medicine Biochemistry Substrate Specificity Analytical Chemistry Hydrolysis Enzyme Carbohydrate Sequence Chromogenic Compounds chemistry biology.protein Humans Amylase alpha-Amylases Alpha-amylase Isopropyl |
| Zdroj: | Carbohydrate Research. 238:109-133 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/0008-6215(93)87008-g |
| Popis: | Twenty-three novel 2-chloro-4-nitrophenyl β- d -maltopentaosides modified at the 6 5 and/or 4 5 position were synthesized as substrates for human alpha amylase. Two human alpha amylases hydrolyzed 6 5 -deoxy-6 5 -, 6 5 - O -, and 4 5 ,6 5 -di- O -substituted derivatives at essentially a single d -glucosidic linkage, but 4 5 ,6 5 - O -bridged and 4 5 - O -substituted derivatives were hydrolyzed at two or more linkages. The amylases displayed smaller K m values for the compounds having hydrophobic modifications. In these derivatives, 2-chloro-4-nitrophenyl O -(6-bromo-6-deoxy-α- d -glucopyranosyl)-(1 → 4)-tris[ O -α- d -glucopyranosy-(1 → 4)]-β- d -glucopyranoside ( 10 ), 2-chloro-4-nitrophenyl O -(6-azido-6-deoxy-α- d -glucopyranosyl)-(1 → 4)-tris[ O -α- d -glucopyranosyl-(1 → 4)]-β- d -glucopyranoside ( 19 ), and 2-chloro-4-nitrophenyl O -[6- O -( N -isopropyl)carbamoyl-α- d -glucopyranosyl]-(1 → 4)-tris[ O -α- d -glucopyranosyl-(1 → 4)]-β- d -glucopyranoside ( 30 ), which were rapidly hydrolyzed by the two amylases at a limited position at an approximately equal rate, were shown to be very useful blocked-type substrates for assay of human alpha amylase. |
| Databáze: | OpenAIRE |
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