Add time:07/27/2019         Source:sciencedirect.com

The formation of an enzyme-inhibitor adduct between bovine trypsin and [2-13C]p-amidinophenylpyruvic acid has been investigated by 13C NMR spectroscopy. The observation of a resonance at 100.8 ppm demonstrates that the hemiketal formed between the hydroxyl of serine-195 and the 2-13C carbon of p-amidinophenylpyruvic acid is sp3 hybridized with no significant deviation from tetrahedral geometry. It is shown that stabilization of the hemiketal oxyanion if it occurs is less effective than in chloromethylketone inhibitor complexes. The tetrahedral adduct is stable from pH 3 to 8. The mechanisms of breakdown of the tetrahedral adduct at pH extremes are discussed.

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