Enantioselective inhibition of human leukocyte elastase.
(RS)-Diethyl-2-benzyl-succinate was resolved using alpha-chymotrypsin. The two enantiomers were then elaborated to yield (S)-(+) and (R)-(-)-3-benzyl-N-[(methyl-sulfonyl)oxy]succinimide and the inhibitory activity of the two enantiomers toward human leukocyte elastase was subsequently determined. The k2/KI values for the R and S isomers were found to be 330 and 1500 M-1 s-1, respectively.
Groutas
W C
WC
Department of Chemistry, Wichita State University, Kansas 67208.
Brubaker
M J
MJ
Venkataraman
R
R
Stanga
M A
MA
D002918:Chymotrypsin; D006801:Humans; D007700:Kinetics; D019272:Leukocyte Elastase; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry / Q000494:pharmacology*
D013388:Succinimides; C051109:3-benzyl-N-(methanesulfonyloxy)succinimide; D002918:Chymotrypsin; D010196:Pancreatic Elastase; D019272:Leukocyte Elastase