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Issue 34, 2013
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The relative hydrolytic reactivities of pyrophosphites and pyrophosphates

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Abstract

The pH-rate profiles for the hydrolysis of pyrophosphate (PP(V)) and pyrophosphite (PP(III), pyro-di-H-phosphonate) are a complex function of pH, reflecting the different ionic species and their relative reactivities. PP(III) is more reactive than PP(V) at all pHs and only PP(III) shows a hydroxide-ion reaction at high pH, so it is 1010-fold more reactive than PP(V) in 0.1 M NaOH. The pKa2 of PP(III) ∼0.44, so the dominant species at pH's > 1 is the di-anion PP(III)2−. Although there is no observable (NMR or ITC) binding of Mg2+ to the PP(III) di-anion there is a modest increase in the rate of hydrolysis of PP(III) by Mg2+. PP(III) is neither a substrate nor an inhibitor of pyrophosphatase, the enzyme that efficiently catalyses the hydrolysis of PP(V).

Graphical abstract: The relative hydrolytic reactivities of pyrophosphites and pyrophosphates

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Publication details

The article was received on 16 Apr 2013, accepted on 16 Jul 2013 and first published on 16 Jul 2013


Article type: Paper
DOI: 10.1039/C3OB40755A
Citation: Org. Biomol. Chem., 2013,11, 5727-5733
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    The relative hydrolytic reactivities of pyrophosphites and pyrophosphates

    D. Mistry and N. Powles, Org. Biomol. Chem., 2013, 11, 5727
    DOI: 10.1039/C3OB40755A

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