Analytical Biochemistry 1986-02-15

Single-step, quantitative derivatization of amino, carboxyl, and hydroxyl groups in iodothyronine amino acids with ethanolic pivalic anhydride containing 4-dimethylaminopyridine.

M Joppich, R Joppich-Kuhn, A Sentissi, R W Giese

Index: Anal. Biochem. 153(1) , 159-65, (1986)

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Abstract

Reaction of thyroxine with ethanol and pivalic anhydride in the presence of 4-dimethylaminopyridine quantitatively forms N,O-dipivalyl thyroxine ethyl ester. Other iodothyronines react similarly and the procedure is moisture insensitive. Apparently this reaction is successful, in contrast to similar procedures reported for the derivatization of alpha-amino acids, because it overcomes the problem in other procedures of irreversible side reactions arising from an oxazolone intermediate.