Optimization of lipase-catalyzed glucose ester synthesis in ionic liquids

Ha, Sung Ho; Hiệp, Nguyễn Minh; Lee, Sang Hyun; Koo, Yoon‐Mo

doi:10.1007/s00449-009-0363-4

Cited by 40 publications

(27 citation statements)

References 18 publications

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“…The effect of reaction temperature on the v app and molecular weight in the Novozym 435 catalyzed synthesis of poly(1'‐ O ‐3‐hydroxyacyl‐sucrose) in chloroform‐DMSO ratio 4:1 (v/v) was observed (Table ). It has been previously stated that in micro‐aqueous sugar ester synthesis, the solubility and rate of sugar dissolution play an important role in product yield . In fact, in such reaction, the solubility of sugar moiety has been reported to largely rely on the reaction temperature and solvent polarity .…”

Section: Resultsmentioning

confidence: 99%

Single‐step lipase‐catalyzed functionalization of medium‐chain‐length polyhydroxyalkanoates

Gumel

Annuar

Heidelberg

2012

J of Chemical Tech & Biotech

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BACKGROUND: Functionalization of aliphatic biopolymers such as bacterial polyhydroxyalkanoates (PHA) using biologically active hydrophilic moieties like sugars helps to improve the hydrophilicity and biodegradability of the biomaterial. RESULTS: The effects of reaction variables reaction time, temperature, enzyme concentration and substrate ratio on reaction rate and yield in the synthesis of poly(1'-O-3-hydroxyacyl-sucrose) usingCandida antarctica lipase B (EC 3.1.1.3) were studied. Using H 2 O 2 as micro-initiator, enzyme-mediated synthesis yielded reaction rate, v app of 0.076 x 10 −5 mol L −1 s −1 . The biodegradability of the functionalized polymer was observed to increase by 1.5 fold compared with the non-functionalized material apart from showing better compostability. Increasing the reaction temperature (>50 • C), enzyme concentration (>15 g L −1 ) and reactant ratio (w/w) of sucrose:PHA (>2) did not increase further the rate or yield. The sucrose-functionalized mcl-PHA was characterized with respect to the non-functionalized material. CONCLUSIONS: Novozym  435 can be used effectively to synthesize poly(1'-O-3-hydroxyacyl sucrose) in micro-aqueous medium bypassing the need for chemo-synthetic steps. The synthesized biomaterials have potential applications in biomedical and industrial niches.

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Section: Resultsmentioning

confidence: 99%

Single‐step lipase‐catalyzed functionalization of medium‐chain‐length polyhydroxyalkanoates

Gumel

Annuar

Heidelberg

2012

J of Chemical Tech & Biotech

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“…ILs have also been used in the chemical synthesis of sugar esters . Moreover, many of them have been found to stabilize enzymes and consequently, ILs and mixtures of ILs and organic solvents have been successfully used in the enzymatic synthesis of different glucose esters .…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of epoxy fatty acid starch ester in ionic liquid–organic solvent mixture from vernonia oil

et al. 2013

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In this study, epoxy fatty acid esters of cassava starch were synthesized by reacting cassava starch with vernonia oil methyl ester (epoxy ester) using 1-butyl-3-methylimidazolium hexafluorophosphate, [C 4 C 1 Im][PF 6 ] ionic liquid (IL) as a reaction medium and DMSO as co-solvent. Lipase Candida antarctica fraction B (Novozyme 435) was used as a catalyst for the esterification reaction. In the optimized reaction conditions, a degree of substitution (DS) of 0.95 was achieved, at a reaction temperature of 40°C within 72 h of reaction time. The new cassava starch esters were characterized by infrared (FTIR), solid state NMR (CP/MAS 13 C NMR), SEM, XRD, thermogravimetric analysis (TGA), and DSC. FTIR and NMR spectroscopy analyses confirmed the successful esterification of starch and the DS was calculated to be 0.95 by titration methods. SEM and XRD studies showed that the morphology and crystallinity of native cassava starch were significantly changed upon esterification producing a continuous and amorphous material. Finally, the thermal behavior of the native and the starch vernolate was investigated using TGA and DSC techniques. The results revealed a change in the characteristic melting point and decomposition pattern of the new polymer. The onset decomposition temperature of the new starch vernolate is similar to the native form.

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“…As is known, the enzyme displays a high level of activity for sugar ester synthesis . However, it has been reported that the formation of carbamates by scCO 2 and the free amine groups on the surface of the enzyme can deactivate the enzyme .…”

Section: Resultsmentioning

confidence: 99%

Lipase‐catalyzed Synthesis of Sugar Ester in Mixed Biphasic System of Ionic Liquids and Supercritical Carbon Dioxide

Chang

Zhang

Tang

2017

J Chinese Chemical Soc

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Lipase‐catalyzed synthesis of lauroyl glucose ester was continuously performed in a biphasic system consisting of supercritical CO2 and an ionic liquid (IL). Fourier transform infrared spectroscopy and nuclear magnetic resonance spectroscopy are employed to identify the product lauroyl glucose ester. The effects of reaction pressure, temperature, substrate flow rate, the amount of enzyme, and the amount of IL on the glucose conversion rate are investigated. The highest glucose conversion of up to 95.5% could be achieved at the optimal condition, which is higher than that in the pure IL. The enzyme activity in the biphasic system was 18.19 μmol/g/min, which is much higher than that in the pure IL. The continuous reaction in the binary system could last for 10 h at high enzyme activity. The combination of supercritical CO2 and ILs could not only improve the reaction rate and yield, which are attributed to the fast mass transfer rate and enhanced enzyme activity and lifespan, but also make the product separation and enzyme/ILs recycling easier.

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Optimization of lipase-catalyzed glucose ester synthesis in ionic liquids

Cited by 40 publications

References 18 publications

Single‐step lipase‐catalyzed functionalization of medium‐chain‐length polyhydroxyalkanoates

Single‐step lipase‐catalyzed functionalization of medium‐chain‐length polyhydroxyalkanoates

Enzymatic synthesis of epoxy fatty acid starch ester in ionic liquid–organic solvent mixture from vernonia oil

Lipase‐catalyzed Synthesis of Sugar Ester in Mixed Biphasic System of Ionic Liquids and Supercritical Carbon Dioxide

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