Lipase catalysed acylation of hydroxylamine and hydrazine derivatives

The lipase catalysed acylation of hydroxylamine-and hydrazine as well as their derivatives by octanoic acid is very efficient. Cross-linked crystals of Candida rugosa lipase (ChiroCLEC-CR) mediated the conversion of racemic ibuprofen into (S)-ibuproxam. A number of lipases also catalysed the condensation of hydrazine with an excess of octanoic acid giving N,N′-dioctanoylhydrazine. The hydrazide of 2-(4-isobutylphenyl)propanoic acid (ibuprofen), prepared by non-enzymatic reaction of ibuprofen methyl ester with hydrazine, acted as nucleophile towards several lipases that do not accept ibuprofen derivatives as acyl donor.