• Journal of the Korean Applied Science and Technology
• /
• v.15 no.4
• /
• pp.45-56
• /
• 1998

Methyl fructoside oleic acid polyester(MFPE), fructose-based sugar polyester, was synthesized by solvent-free, soap-free transesterification of methyl oleate with methyl fructoside(MF) as a sugar starting material in the presence of conventional potassium carbonate basic catalyst. Methyl fructoside was found to be an effective sugar starting material, because of its low softning point, high heat stability, high miscibility, and high reactivity than other sugars. Yield 98% of purified MFPE based on initial weight of MF was obtained at 1:5 of the molar ratio of methyl fructoside to methyl oleate, 2%(w/w) of potassium carbonate catalyst content, 20${\sim}$200mmHg of reduced pressure and $180^{\circ}C$ of reaction temperature. MFPE structure was confirmed by infrared and proton nuclear magnetic resonance spectroscopy. Physical properties of methyl of fructoside oleic acid polyester such as viscosity, HLB, solubility, color, refractive index, specific gravity, and density were similar to physical properties of sucrose polyesters(SPE) and vegetable oils. Then, it was elucidated that MFPE was sufficient to replace the SPE and conventional oils.

• KSBB Journal
• /
• v.13 no.6
• /
• pp.706-717
• /
• 1998

Enzymatic synthesis of fructose-based sugar fatty acid esters, such as methyl fructoside oleic acid mono and diester, was investigated using methyl fructoside as a sugar starting material. For the production of methyl fructoside fatty acid monoester by solvent process, 2-methyl 2-propanol was found to be a god reaction medium resulting a higher yield and productivity due to its high sugar solubility. The yield and productivity of methyl fructoside oleic acid monoester were 70% and 12.6g/L-hr, respectively, when molar ratio of methyl fructoside, initial concentration of methyl fructoside, enzyme(Novozym 435) content, and reaction temperature were 3:1, 200g/L, 1%(w/v), and $60^{\circ}C$, respectively. Methyl fructoside oleic acid diester was prepared by lipase-catalyzed diacylation of methyl fructoside and oleic acid in the solvent-free process. Maximum yield of 98% and productivity of 140g/L-hr were achieved when molar ratio(methyl fructoside and oleic acid) of 1:2 enzyme content of 10%(w/v) and reaction temperature of $70^{\circ}C$ were applied for the operating conditions under a reduced pressure of 20∼200 mmHg.

• Journal of Korean Ophthalmic Optics Society
• /
• v.5 no.1
• /
• pp.89-94
• /
• 2000

Methyl fructoside acrylate and methacrylate were synthesized by lipase-catalyzed glycosylation of acrylic acid, methacrylic acid and vinyl methacrylate with ${\beta}$-methyl fructoside in t-butanol as a reaction medium. From the optimum conditions of enzymatic synthesis for acrylate and methacrylate, we obtained 78% conversion for methyl fructoside acrylate and 93% conversion for methyl fructoside methacrylate. The polymerizable sugar acrylates have potential application as biomedical polymer such as hodrogel contact lens.

• KSBB Journal
• /
• v.11 no.5
• /
• pp.529-535
• /
• 1996

Methyl frucloside was purified from the aqueous sugar/methyl fructoside solution by liquid chromatography using Amberlite IRA-900, strong anion-exchange resin. The optimum operating conditions, resolution and productivity of methyl fructoside were discussed to evaluate the practical feasibility of the proposed chromatographic separation process of methyl fructoside which is useful as a new starting material for sugar ester synthesis. The linear chromatography model with HETP was well applied to the chromatographic separation process of methyl fructoside and the theoretical solution successfully predicted the elution chromatogram of methyl fructoside and sucrose at different superficial linear velocity of eluent for rectangular feed with different loading volume of packed bed. The optimum operating conditions were found to be 75% with the loading volume of packed bed at 1.13 cm/min of the superficial linear velocity at $60^{\circ}C$, and gave the productivity of methyl fructoside of 7 mg/g-resin/h with the resolution of 1.1.

• Journal of the Korea Safety Management & Science
• /
• v.1 no.1
• /
• pp.259-272
• /
• 1999

In order to enhance the selectivity, productivity and yield of methyl fructoside, which was synthesized by enzymatic glycosylation of sucrose and methanol solution, controlling of surface property of solid support using different immobilization procedures optimized microenvironment of immobilized invertase. Silanization and polyethylene imine coating methods were adopted to give a hydrophobic and hydrophilic environment of immobilized invertase. As a result, polyethyleneimine coating method gave higher loading of enzyme, effective activity, and relative activity than silanization method, because it brought on increasing the functional density of amino group and enhancing the conservation of activity by regulating of hydrophilicity. And then, hydrophilic environment was possible to restraint the assessing of methyl fructoside molecule, which was more hydrophobic than sucrose, fructose, and glucose molecule in the reaction mixture, into .the active site of immobilizedinvertase. Consequently, hydrophilic microenvironment of immobilized invertase by polyethyleneimine coating obtained higher yield and productivity with increasing conversion than silanized and native invertase. Thus, this procedure optimized the microenvironment of immobilized invertase suitable for the enzymatic synthesis of methyl fructoside.

• KSBB Journal
• /
• v.10 no.2
• /
• pp.159-165
• /
• 1995

Methyl fructoside was continuously produced in suspended bed enzyme reactor using alginate-enclosed microspheres biocatalyst which was developed for enzymatic synthesis of methyl fructoside. And the continuous operating conditions were optimized with reactor simulation in order to demonstrate a feasibility of commercialization of the continuous enzymatic production process development. The yield and productivity of methyl fructoside were as high as 47.1%o and $2g/\ell$-hr, respectively. The optimum operating conditions were pH 4.8, 30%(v/v) of methanol content and $2U/m\ell$ of enzyme activity when the initial concentration of sucrose is $0.291mo1/\ell$ at the reaction temperature of $25^{\circ}C$.

• Journal of the Korean Applied Science and Technology
• /
• v.19 no.2
• /
• pp.137-144
• /
• 2002

Methyl glycoside oleic acid polyester was successfully prepared from methyl glycosides and methyl oleate by emulsion interesterification in the presence of methyl fructoside oleic acid polyester as an emulsifier. Emulsion interesterification process was optimized to obtain 98% yield of methyl glycoside polyester within $3{\sim}5hr$ at temperatures as relatively low as $90{\sim}150^{\circ}C$ and $20{\sim}200mmHg$ pressure with a five-fold molar ratio of oleic acid methyl ester to methyl glycoside in the presence of 2(w/w)% potassium carbonate and 2O(v/v)% methyl fructoside polyester based on oleic acid methyl ester.

• KSBB Journal
• /
• v.8 no.4
• /
• pp.313-319
• /
• 1993

Methyl fructoside was synthesized from sucrose and methanol using an immobilized invertase. The enzyme was covalently bound by glutaraldehyde on porous silica coated with polyethyleneimine to give loading capacity of 120mg of invertase per one gram of dry porous silica and effective activity of 100U per one milligram of bound invertase. Polyethyleneimine coating imparted a hydrophillic character, good activity retention and high loading capacity to the surface of porous silica as well as hydrophillic microenviroment in the vicinity of bound invertase. The immobilized enzyme was formed into an alginate-enclosed silica bead to have enough activity for methyl fructoside synthesis from aqueous methanol-sucrose solution. Using the alginate-enclosed biocatalyst the yield of methyl fructoside was obtained as high as 55.9% from aqueous 30% (v/v) methanol and 0.291mo1/l sucrose with 2U/ml activity at $25^{\circ}C$, pH 4.8.

• KSBB Journal
• /
• v.16 no.1
• /
• pp.82-86
• /
• 2001

Glyco-acrylate and methacrylate were synthesized by lipase-catalyzed glycosylation of acrylic acid, methacrylic acid and their vinyl esters with $\beta$-methyl fructoside and glycerol in t-butanol as a reaction medium. At the optimum conditions for enzymatic glycosylation of acrylic acid and vinyl methacrylate, we attained up to 80% conversion for glyco-acrylate from acrylic acid and 90% conversion for glyco-methacrylate from vinyl methacrylate. The polymerizable glyco-acrylates and methacrylate have biomedical application as hydrophilic monomers and hydration modifiers to be use for hydrogel contact lens formulation.

• KSBB Journal
• /
• v.8 no.4
• /
• pp.320-327
• /
• 1993

Latex microspheres of styrene/acryl copolymer with acrylamide functional group were used for the stable covalent immobilization of an enzyme applicable for enzymatic synthesis of glycoside. The latex microspheres were coated with polyethyleneimine to establish structural and functional properties relevant to the covalent Immobilization with a high retention of activity. Polythyleneimine-coated microspheres satisfactorily immobilized the invertase for methyl fructoside synthesis, and model reaction were formed into alginate-enclosed microspheres biocatalyst. Using the alginate-enclosed microspheres biocatalyst, the yield of model glycoside was obtained as high as 52.2% at concentration of aqueous 30%(v/v) methanol and 0.291mo1/1 sucrose solution with 2U/ml of activity. The present study showed that the latex microspheres were successfully applied to enzymatic synthesis of glycoside.