Chemo-enzymatic synthesis of N-arachidonoyl glycine.
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.
Goujard
L
L
UMR IATE, CIRAD-AMIS, Lipotechny Laboratory, TA 40/16, 73 rue JF Breton, 34398 Montpellier cedex 5, France.
Figueroa
M C
MC
Villeneuve
P
P
D016718:Arachidonic Acid / Q000737:chemistry*; D001095:Arachidonic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D004789:Enzyme Activation; D005656:Fungal Proteins; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry* / Q000145:classification; D034442:N-substituted Glycines / Q000737:chemistry; D013379:Substrate Specificity
D001095:Arachidonic Acids; D005656:Fungal Proteins; C465623:N-arachidonylglycine; D034442:N-substituted Glycines; D016718:Arachidonic Acid; D008049:Lipase; C431349:lipase B, Candida antarctica; D005998:Glycine