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It has been shown that L-tyrosine 0-sulphate, a component of mammalian fibrinogens, is not desulphated to any appreciable extent by the rat (Dodgson, Powell & Tudball, 1960). However, the ester is metabolized to yield two major products, one of which has been identified as the sulphate ester of p-hydroxyphenylacetic acid (Dodgson, Powell, Rose & Tudball, 1961). The latter compound was eliminated in an unchanged form when injected into rats and the possibility therefore existed that the unidentified metabolite was the sulphate ester of p-hydroxyphenylpyruvic acid, a probable intermediate on the pathway between L-tyrosine 0-sulphate and p-hydroxyphenylacetic acid sulphate. However, this could not be confirmed because an authentic sample of the ester could not be prepared. p-Hydroxyphenylpyruvic acid readily undergoes spontaneous conversion into p-hydroxyphenylacetic acid (Bloxam, Day, Gibbs & Woolf, 1960) and p-hydroxybenzaldehyde (Doy, 1960) but the sulphate ester has been prepared by modifying the standard procedure (Burkhardt & Lapworth, 1926) so that mildly acidic conditions were maintained throughout. Under such conditions the ester sulphate linkage and the labile oc-oxo acid side chain were reasonably stable. The present work describes this preparation and also shows that the sulphate ester exhibits behaviour similar to the parent phenol with respect to the lability of the a-oxo acid side chain.

Studies on l-tyrosine O-sulphate. 1. Preparation and properties of potassium p-hydroxyphenylpyruvic acid [35S]sulphate