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Role of Lysine in Catalysing Ester Hydrolysis

Abstract

IN their criticism of our paper1, Chesbro and Hedrick make some points that are indeed well taken. Their objection to the implication that bond-strength is a function of pH is undoubtedly valid. However, the statement they quote from our paper does not; imply such a functional relationship. Rather, we had in mind the stretching of the N—H bond which may be expected to occur before the bond breaks (more so the more alkaline the environment) and which certainly will allow the proton to function more effectively as an acidic catalyst. It is regretted that for the sake of brevity we were not explicit enough to forestall a mistaken implication.

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References

  1. Gero, A., and Withrow, C. L., Nature, 180, 1354 (1957).

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  2. Bender, M. L., and Turnquest, B. W., J. Amer. Chem. Soc., 79, 1652, 1656 (1957).

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GERO, A. Role of Lysine in Catalysing Ester Hydrolysis. Nature 183, 994–995 (1959). https://doi.org/10.1038/183994b0

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