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Pyridoxal Phosphate and Catalysis

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Question: Pyridoxal phosphate is required for transamination reactions. The mechanism of catalysis by pyridoxal phosphate can be studied free of enzyme, since pyridoxal itself (shown in attachment) is active towards substrates in the presence of a metal ion (the rate is significantly reduced, but can be measured). Consequently, one can study changes in pyridoxal phosphate structure on catalysis. Based on your understanding of the mechanism of action by pyridoxal phosphate, which of the analogues below would you expect to be active, and which would be inactive? Explain your answer.

See attachment to view the analogues.

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Solution Summary

This solution provides a detailed explanation of how to approach this biochemistry-based problem. A description of each analog is also provided, to illustrate whether or not it is active or inactive.

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Pyridoxal phosphate has a number of unique features that are important for its functioning.

(1) The aldehyde group at C4 of the ring is critical for forming the Schiff base with an amino group. All analogues have this feature, so that's not a problem with any of them.

(2) At pH 7.0, the C3 hydroxyl group is ionized. This ...

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