Enzymatic synthesis of carbohydrate esters of fatty acid (I) esterification of sucrose, glucose, fructose and sorbitol

Abstract

The authors attempted to synthesize carbohydrate esters of fatty acids enzymatically in order to overcome the problems associated with the chemical processes for the synthesis of commercial sucrose esters. The enzymes used were lipases from microorganisms belonging to Rbyzopus, Enterbacterium, Aspergillus, Pseudomonas, Cbromobacterium, Candida, Mucor and Penicillium. Fatty acids (stearic, oleic and linoleic) and carbohydrates (sucrose, glucose, fructose and sorbitol) used for the reaction were obtained from commercial sources. The enzyme reaction was performed by mixing the enzyme and the substrates in the buffer solution and incubating at 40 C; after freeze-drying the mixture, the products were extracted and subjected to thin layer chromatography (TLC) and high performance liquid chromatography (HPLC). It was observed by TLC and HPLC that carbohydrate esters of fatty acid were produced by the enzyme reaction, and their structures were confirmed by infra red (IR) and nuclear magnetic resonance (NMR) spec-trometries~ The lipase from Candida cylindracea was the most enzyme active on the synthesis of carbohydrate esters. The optimum conditions for its activity were as follows: molar ratio of carbohydrate to fatty acid: O.05mol/1 : 0.2reel/I; amount of lipase: 4g/l; pH of the reaction mixture: 5.4 in phosphate buffer; reaction period: 72 hr.

Enzymatic synthesis of esters in organic medium with lipase from Byssochlamys fulva

“…Stearic acid, oleic acid, and linolenic acid gave 26.2%, 24.4% and 42.4% of esterification, respectively, under similar reaction conditions. Seino et al (1984) reported that linoleic acid and oleic acid yielded a higher amount of esters than stearic acid by lipase from Candida cylindracea. The lipase from B. fulva had a higher extent of specificity towards the triglycerides containing linoleic acid in an aqueous solution (Ku & Hang, 1994).…”

Investigation of a New Natural Particleboard Adhesive Composed of Tannin and Sucrose. 2. Effect of Pressing Temperature and Time on Board Properties, and Characterization of Adhesive

“…Disappearance of two absorption peaks at around 1130 cm -1 and 920 cm -1 was observed. Those peaks were attributed to the glycosidic linkage (C-O-C) contribution (Kacurakova et al 2000) and pyranose ring of sucrose (Seino et al 1984). This indicated the decomposition of sucrose.…”

Esterification of Glycosides with Glycerol and Trimethylolpropane Moieties byCandida cylidraceaLipase

“…To obtain monoglucosylated transfer product, the solution was then treated with Aspergillus sp. glucoamylase (6,200 unit, a partially purified preparation obtained from Glucozyme NEO XL-128, Nagase Biochemicals Co.) at 40°C for 2 hr. Glc-TMP, Gal-TMP, and Frc-TMP finally isolated were 1120 mg, 699 mg, and 329 mg, respectively.…”

“…2 -5) It has also been reported that esters of sorbitol and several carbohydrates were synthesized in aqueous reaction systems. 6,7) Specific and efficient esterification of alkyl glucosides by immobilized Candida antarctica lipase has been reported recently. 8) To improve the reactivity of carbohydrates with lipase and the selectivity of hydroxyl groups to be esterified, we synthesized several kinds of glycosides, the reducing ends of which were glycerol and 2-ethyl-2-(hydroxymethyl)-1,3-propanediol (trimethylolpropane, TMP), by enzymatic transglycosylation.…”