Chemo-enzymatic synthesis of N-arachidonoyl glycine

Goujard Laurent, Figueroa-Espinoza Maria-Cruz, Villeneuve Pierre. 2004. Chemo-enzymatic synthesis of N-arachidonoyl glycine. Biotechnology Letters, 26 (15) : 1211-1216.

https://doi.org/10.1023/B:BILE.0000036597.25673.33

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Résumé : 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 Agrovoc : glycine (acide aminé), acide arachidonique, biocatalyseur, butyrate (ester), synthèse chimique, estérase, activité enzymatique, Candida albicans, acylation, lipase

Mots-clés complémentaires : Synthèse enzymatique

Classification Agris : Q02 - Traitement et conservation des produits alimentaires
Q60 - Traitement des produits agricoles non alimentaires

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