You discovered an enzyme that catalyzes the hydrolysis of the C-P bond of phosph

Question

You discovered an enzyme that catalyzes the hydrolysis of the C-P bond of phosphonoacetaldehyde (note: this is NOT a phosphate, but a phosphonate). When chiral [17O, 18O] thiophosphonoaldehyde is used as a substrate, the phosphate produced has its stereochemistry retained. (Double displacement?)

Incubation of the enzyme with substrate and sodium borohydride inactivates the enzyme (no inactivation occurs in the absence of substrate). If NaBH4 (radioactive hydrogen) is used and the enzyme is analyzed, the tritium as part of a modified amino lysine residue. Draw the mechanism that is compatible with all of these results.

Explanation / Answer

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