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Chemo-enzymatic synthesis of N-arachidonoyl glycine

Goujard L., Figueroa-Espinoza M.C., Villeneuve P.. 2004. Biotechnology Letters, 26 (15) : p. 1211-1216.

DOI: 10.1023/B:BILE.0000036597.25673.33

N-Arachidonoyl glycine was synthesized in a chemo-enzymatic process where glycine tert-butyl ester was acylated by arachidonic acid and the resulted ester was then de-protected to give the final product. Among various lipases tested and chosen for their ability to cleave fatty amides, that from Candida antarctica B gave the best results resulting in a 39% hydrolysis after 24 h. This enzyme was then used for the reverse N-acylation synthesis and gave a 75% product formation after 24 h using methyl ester of arachadonic acid as acyl donor and acetonitrile as solvent. Direct acylation of glycine gave less than 10% yield.

Mots-clés : glycine (acide aminé); acide arachidonique; biocatalyseur; butyrate (ester); synthèse chimique; estérase; activité enzymatique; candida albicans; acylation; lipase; synthèse enzymatique

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