Synthesis of 4-Aminophenyl N-Acetyl-β-D-glucosaminide Derivatives and Their Application to the Rate-Assay of N-Acetyl-β-D-glucosaminidase

• 葛西 浩一

  Research and Development Division, Kikkoman Corporation

• 岡田 清

  Research and Development Division, Kikkoman Corporation

• 山次 信幸

  Research and Development Division, Kikkoman Corporation

抄録

Four N-acetyl-β-D-glucosaminides, 4-amino-2,6-dibromophenyl (1a), 4-amino-2,6-dichlorophenyl (1b), 4-amino-2-chlorophenyl (1c) and 4-aminophenyl N-acetyl-β-D-glucosaminides (1d) were synthesized. Substrates 1a-c were hydrolyzed by N-acetyl-β-D-glucosaminidase and the released aglycones reacted with N-ethyl-N-(3-methylphenyl)-N'-succinylethylenediamine to produce indoaniline dyes in the presence of bilirubin oxidase under weakly acidic rate-assay conditions (pH 5.0). The K_m values for 1a-c were 1.97,1.65 and 1.39 mM, respectively. Among these compounds, 1b is considered to be the substrate with most potential for the rate-assay of N-acetyl-β-D-glucosaminidase, since it showed the largest V_<max> value and the strongest color generation from colorless to green (λ_<max> 302→718 nm)following enzyme hydrolysis and the coupling reaction. Furthermore, 1b was moderately soluble and stable in aqueous solution and exhibited about a 5.9-fold higher sensitivity to the enzyme than 2-chloro-4-nitrophenyl N-acetyl-β-D-glucosaminide.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 43 (2), 266-270, 1995-02-15

  公益社団法人日本薬学会

キーワード

• N-acetyl-β-D-glucosaminidase
• rate-assay
• enzyme activity
• 4-aminophenyl N-acetylβ-D-glucosaminide

詳細情報

• CRID: 1571417127325145344
• NII論文ID: 110003631454
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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