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

Research output: Contribution to journalArticle

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 - Jan 1 1996
Externally publishedYes

Fingerprint

Boronic Acids
Chymotrypsin
Sugars
Screening
Fluorescence
Acids
Enzyme activity
Carboxylic acids
Hydrolysis
Polyols
Peptide Hydrolases
Naphthalene
Glucose
Water

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Screening of boronic acids for strong inhibition of the hydrolytic activity of α-chymotrypsin and for sugar sensing associated with a large fluorescence change. / Suenaga, Hikaru; Yamamoto, Hiromasa; Shinkai, Seiji.

In: Pure and Applied Chemistry, Vol. 68, No. 11, 01.01.1996, p. 2179-2186.

Research output: Contribution to journalArticle

@article{6ad44cce6fbf4662809895581011133c,
title = "Screening of boronic acids for strong inhibition of the hydrolytic activity of α-chymotrypsin and for sugar sensing associated with a large fluorescence change",
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.",
author = "Hikaru Suenaga and Hiromasa Yamamoto and Seiji Shinkai",
year = "1996",
month = "1",
day = "1",
doi = "10.1351/pac199668112179",
language = "English",
volume = "68",
pages = "2179--2186",
journal = "Pure and Applied Chemistry",
issn = "0033-4545",
publisher = "IUPAC Secretariat",
number = "11",

}

TY - JOUR

T1 - Screening of boronic acids for strong inhibition of the hydrolytic activity of α-chymotrypsin and for sugar sensing associated with a large fluorescence change

AU - Suenaga, Hikaru

AU - Yamamoto, Hiromasa

AU - Shinkai, Seiji

PY - 1996/1/1

Y1 - 1996/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0001755257&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001755257&partnerID=8YFLogxK

U2 - 10.1351/pac199668112179

DO - 10.1351/pac199668112179

M3 - Article

AN - SCOPUS:0001755257

VL - 68

SP - 2179

EP - 2186

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

IS - 11

ER -