Royal Society Publishing

Stereochemistry of Phosphoryl Transfer

G. Lowe , P. M. Cullis , R. L. Jarvest , B. V. L. Potter , B. S. Sproat

Abstract

A general method has been developed for the synthesis of chiral [<latex>$^{16}$</latex>O, <latex>$^{17}$</latex>O, <latex>$^{18}$</latex>O] phosphate monoesters of known absolute configuration. An analytic method for determining the absolute configuration of chiral phosphate esters has also been developed, which is based on the isotope effects of <latex>$^{17}$</latex>O and <latex>$^{18}$</latex>O at phosphorus in the <latex>$^{31}$</latex>P nuclear magnetic resonance spectrum. These methods have shown that phosphoryl transfer catalysed by hexokinase, phosphofructokinase and pyruvate kinase occurs with inversion of configuration. This is most simply interpreted as an `in-line' transfer of the phosphoryl group between substrates in the enzyme-substrate ternary complex.

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