Inhibition of serine proteases by arylboronic acids.

Proceedings of the National Academy of Sciences of the United States of America ·Vol. 68 ·No. 2 ·1971-02-00 ·Pages 478-80

Philipp M, Bender ML

Abstract

Arylboronic acids were found to be strong competitive inhibitors of subtilisin and chymotrypsin. The binding constants are strongly pH dependent and give a Hammett-type plot with a slope of -0.885. The pH dependence, the Hammett plot, and nmr model-system studies indicate that inhibition is due to electron-pair donation by the active site histidine to the bound inhibitor.

MeSH Terms

Bacillus subtilis Benzene Derivatives/pharmacology Binding Sites Boronic Acids/pharmacology Buffers Chymotrypsin/antagonists & inhibitors

Chemicals

Benzene Derivatives Boronic Acids Buffers Chymotrypsin

Authors & Affiliations

2 authors, click to expand affiliations / ORCID

Philipp M

Bender M L

References (6)

6 references, click to expand

n-Alkylboronic acids as bifunctional reversible inhibitors of alpha-chymotrypsin.
FEBS Lett. 1970 Mar 16;7(1):23-25 PMID: 11947420
Spectral studies of the interaction of alpha-chymotrypsin and trypsin with proflavine.
Proc Natl Acad Sci U S A. 1965 Jul;54(1):171-6 PMID: 5216349
A spectrophotometric determination of trypsin and chymotrypsin.
Biochim Biophys Acta. 1955 Apr;16(4):570-5 PMID: 14389277
The reactivity of thiol-subtilisin, an enzyme containing a synthetic functional group.
Biochemistry. 1967 Feb;6(2):610-20 PMID: 6047645
Binding of competitive inhibitors to delta-chymotrypsin in the alkaline pH region. Competitive inhibition kinetics and proton-uptake measurements.
Biochemistry. 1970 Jun 9;9(12):2440-6 PMID: 5423263
Esteratic reactions catalyzed by subtilisins.
J Biol Chem. 1967 Feb 10;242(3):433-6 PMID: 4960646

Article Info

Journal

Proceedings of the National Academy of Sciences of the United States of America

Abbr.

Proc Natl Acad Sci U S A

ISSN

0027-8424

DOI

10.1073/pnas.68.2.478

Published

1971-02-00

Pages

478-80

Language

English

Region

United States

NLM ID

7505876

PMCID

PMC388964

Subset

External Links

PubMed source DOI: 10.1073/pnas.68.2.478 PMC Full Text View journal details

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Inhibition of serine proteases by arylboronic acids.

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