ISSN:
0749-1581
Keywords:
1H NMR
;
Antipain
;
Stereochemistry
;
Cysteine proteases
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Antipain [(1-carboxy-2-phenylethyl)carbamoyl-L-arginyl-L-valyl-DL-arginal] is a potent inhibitor of papain and related proteases. The assignment of 1H NMR signals of the interconverting forms in equilibrium in aqueous solution at pH 5.8 were investigated using two-dimensional DQF-COSY, DOUBLE-RELAYED-COSY, HOHAHA and ROESY nuclear magnetic resonance techniques. The assignments of protons of several forms in equilibrium of the D- and L-arginal antipain isomers were determined in aqueous solution at 300 K, and their corresponding stereochemistry is tentatively proposed. Addition of equimolar amounts of papain resulted in spectral changes and chemical shifts which are compatible with enzyme-L-carbinolamine interactions.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260320406
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