Toward the synthesis of pyroglutamate lauroyl ester: biocatalysis versus chemical catalysis

• Main Authors: Villeneuve, Pierre, Baréa, Bruno, Barouh, Nathalie, Turon, Fabrice, Figueroa-Espinoza, Maria-Cruz, Piombo, Georges, Dhuique-Mayer, Claudie, Pina, Michel
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2004
• Subjects: Q02 - Traitement et conservation des produits alimentaires; Activité enzymatique; Ester; Acide glutamique; Synthèse chimique; Candida; Biocatalyseur; Estérase; Enzyme; Échange d'ion; Lipase; http://aims.fao.org/aos/agrovoc/c_2604; http://aims.fao.org/aos/agrovoc/c_2671; http://aims.fao.org/aos/agrovoc/c_3291; http://aims.fao.org/aos/agrovoc/c_28580; http://aims.fao.org/aos/agrovoc/c_1247; http://aims.fao.org/aos/agrovoc/c_27460; http://aims.fao.org/aos/agrovoc/c_2670; http://aims.fao.org/aos/agrovoc/c_2603; http://aims.fao.org/aos/agrovoc/c_3933; http://aims.fao.org/aos/agrovoc/c_12194; Antarc*; Antarctica
• Online Access: http://agritrop.cirad.fr/518776/; http://agritrop.cirad.fr/518776/1/art%25253A10.1023%25252FB%25253ABILE.0000013710.46900.10.pdf; https://doi.org/10.1023/B:BILE.0000013710.46900.10

The synthesis of dodecyl pyroglutamate (or pyroglutamate lauroyl ester) was achieved in a two-step process involving a pyroglutamic acid alkyl ester intermediate. The reaction was carried out either by lipase or by chemical catalysis using ion exchange resin. Among the various tested lipases, the one from Candida antarctica B gave the best results allowing 73% formation of the desired ester after 6 h. Comparing the efficiency of this latter lipase with the one of Amberlyst IR120H resin in catalyzing this reaction, the biocatalyst gave a molar yield of pyroglutamate lauroyl ester of 79% compared to 69% when using the ion exchange resin starting with 1.04 mmol substrate in each case.