Leucine-phenylalanine dipeptide-based N-mesyloxysuccinimides: synthesis of all four stereoisomers and their assay against serine proteases

Bioorg Med Chem Lett. 1999 Feb 8;9(3):497-500. doi: 10.1016/s0960-894x(99)00017-7.

Abstract

The four stereoisomers of 3-(N-acetylleucylamino)-3-benzyl-1-[(methylsulfonyl)oxy]succinimid e have been prepared and shown to inhibit alpha-chymotrypsin and human neutrophil elastase. The structural and stereochemical features that affect the potency and selectivity of inhibition are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chymotrypsin / antagonists & inhibitors
  • Dipeptides / chemistry
  • Humans
  • Leucine / chemistry*
  • Leukocyte Elastase / antagonists & inhibitors
  • Phenylalanine / chemistry*
  • Serine Proteinase Inhibitors / chemical synthesis*
  • Serine Proteinase Inhibitors / chemistry
  • Serine Proteinase Inhibitors / pharmacology
  • Stereoisomerism
  • Succinimides / chemical synthesis*
  • Succinimides / chemistry
  • Succinimides / pharmacology

Substances

  • Dipeptides
  • Serine Proteinase Inhibitors
  • Succinimides
  • Phenylalanine
  • Chymotrypsin
  • Leukocyte Elastase
  • Leucine