Inhibition of trypsin by t-butyloxycarbonyl-alpha-aza-(4-aminophenyl)alanine phenyl ester.
t-Butyloxycarbonyl-alpha-aza-(4-aminophenyl)alanine phenyl ester (III: R = NH2) has been synthesized. The rate of inhibition of trypsin (EC 3.4.21.4) by this compound (due to acylation followed by slower deacylation) shows a marked pH maximum at approximately 6. The shape of the pH-rate curve is discussed in terms of (i) the normal pH-activity curve of trypsin reacting with a charged substrate, i.e. the protonated form of the amino compound, (ii) the deprotonation of the 4-amino group with pKa 4.3, and (iii) the lower rate of reaction of the enzyme with the uncharged, deprotonated form of the ester.
School of Chemistry, University of Birmingham, UK.
H
H
Din
C J
CJ
Gray
J C
JC
Ireson
R
R
McDonald
D000599:Amino Acids, Diamino / Q000138:chemical synthesis / Q000494:pharmacology*; D007700:Kinetics; D014361:Trypsin Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*
D000599:Amino Acids, Diamino; D014361:Trypsin Inhibitors; C069374:tert-butyloxycarbonyl-alpha-aza-(4-aminophenyl)alanine phenyl ester