Regioselectivity in the reaction of hydrolases with (Z,E)-hexa-2,4-diene-1,6-diol

A good regioselectivity was observed for enzymatic acetylation of (2Z,4E)-2,4-hexadiene-1,6-diol 3 as well as for enzymatic hydrolysis of (2E,4Z)-6-(acetyloxy)-2,4-hexadienyl acetate 6. Finally, (2Z,4E)-6-hydroxy-2,4-hexadienyl acetate 5 was obtained in pure form after two successive acetylations with reversed selectivities. Its regioisomer, (2E,4Z)-6-hydroxy-2,4-hexadienyl acetate 4, was prepared in a pure form by a non biochemical method.