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  • Title: The Lossen rearrangement in biological systems. Inactivation of leukocyte elastase and alpha-chymotrypsin by (dl)-3-benzyl-N-(methanesulfonyloxy) succinimide.
    Author: Groutas WC, Giri PK, Crowley JP, Castrisos JC, Brubaker MJ.
    Journal: Biochem Biophys Res Commun; 1986 Dec 15; 141(2):741-8. PubMed ID: 3643025.
    Abstract:
    (dl)-3-Benzyl-N-(methanesulfonyloxy) succinimide 5 has been found to inactivate human leukocyte elastase and alpha-chymotrypsin efficiently and irreversibly. The kobsd/[I] values were 1170 and 9000 M-1 s-1 respectively. Porcine pancreatic elastase was not inhibited by 5. Compound 5 may constitute the first example of a mechanism-based inhibitor of a serine proteinase that appears to exert its effect via an unprecedented enzyme-induced Lossen rearrangement.
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