Screening of boronic acids for strong inhibition of the hydrolytic activity of α-chymotrypsin and for sugar sensing associated with a large fluorescence change

Hikaru Suenaga, Hiromasa Yamamoto, Seiji Shinkai

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27 Citations (Scopus)

Abstract

The inhibitory effect of arylboronic acids which act as a transition state analogue for certain peptidases is efficiently intensified by added saccharides: this finding enables us to control the enzyme activity by a combination of arylboronic acids and polyols including sugars. In particular, the combined system of 3-biphenylboronic acid and D-glucose strongly inhibited the hydrolysis reaction mediated by α-chymotrypsin, the inhibitory effect (Ki = 1.1×10-7 mol dm-3) being stronger than that of a specific inhibitor, chymostatin (Ki = 4.8×10-7 mol dm-3). Hence, saccharides act as a 'co-inhibitor' in the boronic acid inhibition system. To search for such fluorescent boronic acids that are useful for sensitive detection of sugars in water, 8 aromatic boronic acids have been screened. Among them biphenyl-3-boronic acid and naphthalene-2-boronic acid could fully satisfy three prerequisites for sugar sensing: strong fluorescence intensity, large pH-dependent change in Imax, and shift of the pH-Imax profile to lower pH region in the presence of sugars.

Original languageEnglish
Pages (from-to)2179-2186
Number of pages8
JournalPure and Applied Chemistry
Volume68
Issue number11
DOIs
Publication statusPublished - Nov 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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