A new chromogenic substrate for angiotensin-converting enzyme.
The compound para-nitrobenzyloxycarbonylglycyl-(S-4-nitrobenzo-2-oxa- 1,3-diazole)-L-cysteinylglycine [NO2ZGly(S-NBD)CysGly] with an absorption maximum at 423 nm is readily hydrolyzed by angiotensin-converting enzyme (EC 3.4.15.1. peptidlyldipeptide hydrolase) to yield the S-benzfurazan derivative of cysteinylglycine. An internal S-->N shift occurs immediately to yield the N-benzfurazan derivative which in turn reacts with the sulfhydryl reagent 4,4'-dithiodipyridine to produce the mixed disulfide with an intense absorption at 461 nm. The maximum difference in molar absorptivity of 13,000 M-1 cm-1 occurs at 470 nm.
Department of Chemistry, University of Colorado, Boulder 80309, USA.
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Persson
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Russo
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Wilson
D002863:Chromogenic Compounds / Q000138:chemical synthesis; D006801:Humans; D066298:In Vitro Techniques; D007700:Kinetics; D009578:Nitrobenzenes; D009842:Oligopeptides; D007703:Peptidyl-Dipeptidase A / Q000378:metabolism*; D013053:Spectrophotometry; D013379:Substrate Specificity
D002863:Chromogenic Compounds; D009578:Nitrobenzenes; D009842:Oligopeptides; C115142:nitrobenzyloxycarbonylglycyl-(S-4-nitrobenzo-2-oxa-1.3-diazole)-cycteinylglycine; D007703:Peptidyl-Dipeptidase A