Tetrahedron p. 7587 - 7594 (1997)
Update date:2022-08-11
Topics:
Maugard, Thierry
Remaud-Simeon, Magali
Petre, Dominique
Monsan, Pierre
Enzymatic N-acylation of N-methyl-glucamine (1-deoxy-1-methylamino-D-glucitol) in hexane using lipase from Rhizomucor miehei (Lipozyme) is described. N-methyl-glucamine was solubilized by oleic acid addition which resulted in the formation of an ion-pair between acid and amine function. This ion-pair, identified by Infra-Red spectroscopy, is essential for amide or ester synthesis. Its stability in hexane was also found to be the limiting factor of reaction yield which never exceeded 50% of acid conversion. The chemoselectivity of the reaction between oleic acid and N-methyl-glucamine towards amide or ester synthesis was under the control of acid/amine ratio. This is the first report showing the key role of substrate ionic state shen operating enzyme catalysis in non-conventional media.
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