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3,4-Dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one, a Reagent for Labeling p-Nitrophenyl Esterases with a Chromophoric Reporter Group - Synthesis and Reaction with Chymotrypsin

✍ Scribed by T.M. Kitson; G.H. Freeman

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 489 KB
Volume: 21
Category: Article
ISSN: 0045-2068
DOI: 10.1006/bioo.1993.1030

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✦ Synopsis

We report the synthesis of 3,4-dihydro-3-methyl-6-nitro-2 (H)-1,3-benzoxazin-2-one (DMNB), a close structural analogue of (p)-nitrophenyl dimethylcarbamate. DMNB is unstable in aqueous solution when exposed to light, but is stable in the dark. The compound reacts slowly with chymotrypsin as an analogue of the substrate, (p)-nitrophenyl acetate, and this results in the incorporation of a p-nitrophenol-containing "reporter group" within the enzyme's active site. The (\mathrm{p} K_{i j}) of this group is two (\mathrm{pH}) units higher than that of free (p)-nitrophenol, a result consistent with a hydrophobic environment around the enzymic binding site. Denaturation of the enzyme returns the (\mathrm{p} K_{a}) to its unperturbed value. DMNB has the promise of being a useful active site-directed reagent for other enzymes with p-nitrophenyl esterase activity. 01993 Academic Press. Inc.

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