Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryloyl-2-docosahexaenoyl (or eicosapentaenoyl) glycerol
Autore:
Irimescu, R; Furihata, K; Hata, K; Iwasaki, Y; Yamane, T;
Indirizzi:
Nagoya Univ, Grad Sch Bio & Agrosci, Lab Mol Biotechnol, Nagoya, Aichi 4648601, Japan Nagoya Univ Nagoya Aichi Japan 4648601 hnol, Nagoya, Aichi 4648601, Japan Nippon Suisan Kaisha Ltd, Cent Res Lab, Tokyo 1920906, Japan Nippon SuisanKaisha Ltd Tokyo Japan 1920906 s Lab, Tokyo 1920906, Japan
Titolo Testata:
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
fascicolo: 3, volume: 78, anno: 2001,
pagine: 285 - 289
SICI:
0003-021X(200103)78:3<285:UORMRO>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
POLYUNSATURATED FATTY-ACIDS; DOCOSAHEXAENOIC ACID; ENZYMATIC-SYNTHESIS; STRUCTURED LIPIDS; TRIACYLGLYCEROL STRUCTURE; IN-VIVO; TRIGLYCERIDES; OIL;
Keywords:
1,3-dicapryloyl-2-docosahexaenoyl glycerol; 1,3-dicapryloyl-2-eicosapentaenoylglycerol; esterification; ethanolysis; immobilized Candida antarctica lipase; immobilized Rhizomucor miehei lipase; transesterification; regiospecificity of lipases;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Agriculture,Biology & Environmental Sciences
Citazioni:
15
Recensione:
Indirizzi per estratti:
Indirizzo: Yamane, T Nagoya Univ, Grad Sch Bio & Agrosci, Lab Mol Biotechnol, Nagoya,Aichi 4648601, Japan Nagoya Univ Nagoya Aichi Japan 4648601 ya, Aichi 4648601, Japan
Citazione:
R. Irimescu et al., "Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryloyl-2-docosahexaenoyl (or eicosapentaenoyl) glycerol", J AM OIL CH, 78(3), 2001, pp. 285-289

Abstract

A highly efficient enzymatic method for the synthesis of regioisomericallypure 1,3-dicapryloyl-2-docosahexaenoyl glycerol (CDC) in two steps was established. 2-Monoglyceride (2-MG) formation by ethanolysis of tridocosahexaenoylglycerol (DDD) with immobilized Candida antarctica lipase (Novozym 435)as catalyst was the key step of the synthesis. CDC was finally obtained byreesterification of 2-MG with ethylcaprylate (EtC) catalyzed by Rhizomucormiehei lipase (Lipozyme IM). The regiospecificity of Novozym 435 depended on the type of reaction and the initial composition of the reaction medium. It displayed strict 1,3-regiospecifcity for ethanolysis at a high excess of ethanol in the reaction mixture although it displayed no regiospecificityin transesterification and esterification reactions. The highest yield of CDC (85.4%) was obtained by ethanolysis at a 4:1 weight ratio of ethanol/ DDD for 6 h followed by reesterification at a 20:1 molar ratio of EtC/initial DDD for 1.5 h. The regioisomeric purity of CDC was 100%. Good results were obtained also for the synthesis of 1,3-dicapryloyl-eicosapentaenoylglycerol (CEC) by the same method: 84.2% yield and 99.8% regioisomeric purity at the same reactant ratios as above. The yield of the reesterification step and the regioisomeric purity of the product were influenced by the molar ratio of the reactants for both CDC and CEC syntheses: higher excess of EtC favored higher yields and regioisomeric purity of the products.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/04/20 alle ore 12:57:29