Fluorogenic N-nitrosoamides: active-site labeling reagents for chymotrypsin-like proteases.
Two fluorogenic N-nitrosoamides, N-nitroso-N-((7-methoxycoumarin-4-yl)methyl)-N'-isobutyrylalaninamide (6a) and N-nitroso-N-((6-methoxyquinolin-2-yl)methyl)-N'-isobutyrylalani namide (6b), were synthesized. Both N-nitrosoamides inhibited alpha-chymotrypsin irreversibly; they show promise as labeling reagents for the active sites of chymotrypsin-like proteases.
Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218.
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D001665:Binding Sites; D002918:Chymotrypsin / Q000037:antagonists & inhibitors / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009602:Nitrosamines / Q000138:chemical synthesis* / Q000494:pharmacology; D015363:Quinolones / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
D005456:Fluorescent Dyes; D007202:Indicators and Reagents; C092011:N-nitroso-N-((6-methoxyquinolin-2-yl)methyl)-N'-isobutyrylalaninamide; C092010:N-nitroso-N-((7-methoxycoumarin-4-yl)methyl)-N'-isobutyrylalaninamide; D009602:Nitrosamines; D015363:Quinolones; D002918:Chymotrypsin