Leucine-phenylalanine dipeptide-based N-mesyloxysuccinimides: synthesis of all four stereoisomers and their assay against serine proteases.
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.
Abell
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AD
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Oldham
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MD
D002918:Chymotrypsin / Q000037:antagonists & inhibitors; D004151:Dipeptides / Q000737:chemistry; D006801:Humans; D007930:Leucine / Q000737:chemistry*; D019272:Leukocyte Elastase / Q000037:antagonists & inhibitors; D010649:Phenylalanine / Q000737:chemistry*; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013388:Succinimides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D004151:Dipeptides; D015842:Serine Proteinase Inhibitors; D013388:Succinimides; D010649:Phenylalanine; D002918:Chymotrypsin; D019272:Leukocyte Elastase; D007930:Leucine