Chemo-enzymatic synthesis of N-arachidonoyl glycine

• Main Authors: Goujard, Laurent, Figueroa-Espinoza, Maria-Cruz, Villeneuve, Pierre
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2004
• Subjects: Q02 - Traitement et conservation des produits alimentaires; Q60 - Traitement des produits agricoles non alimentaires; Glycine (acide aminé); Acide arachidonique; Biocatalyseur; Butyrate (ester); Synthèse chimique; Estérase; Activité enzymatique; Candida albicans; Acylation; Lipase; http://aims.fao.org/aos/agrovoc/c_3299; http://aims.fao.org/aos/agrovoc/c_26843; http://aims.fao.org/aos/agrovoc/c_27460; http://aims.fao.org/aos/agrovoc/c_32023; http://aims.fao.org/aos/agrovoc/c_28580; http://aims.fao.org/aos/agrovoc/c_2670; http://aims.fao.org/aos/agrovoc/c_2604; http://aims.fao.org/aos/agrovoc/c_27476; http://aims.fao.org/aos/agrovoc/c_28220; http://aims.fao.org/aos/agrovoc/c_12194; Antarc*; Antarctica
• Online Access: http://agritrop.cirad.fr/523814/; https://doi.org/10.1023/B:BILE.0000036597.25673.33; http://catalogue-bibliotheques.cirad.fr/cgi-bin/koha/opac-detail.pl?biblionumber=184214

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.