Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides

Pedersen, Ninfa Rangel; Wimmer, Reinhard; Emmersen, Jeppe; Degn, Peter; Pedersen, Lars Haastrup

doi:10.1016/s0008-6215(02)00112-x

Cited by 84 publications

(49 citation statements)

References 15 publications

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“…It can be seen that the acetic acid modification led to a slight decrease in the BC crystallinity. This can be explained by the high reactivity of acetic acid compared to hexanoic and dodecanoic acids (Pedersen et al 2002). As already mentioned, the high reactivity of acetic acid can lead to more ester bond formation on BC.…”

Section: Xrd Of Neat and Modified Bcmentioning

confidence: 86%

“…Since the modification reaction did not result in dissolution of BC, the accessible hydroxyl groups for esterification are essentially only at the surface and in the amorphous regions of the BC. The more intense 1750 cm -1 adsorption band in C 2 -BC is caused by the higher reactivity of acetic acid compared to hexanoic and dodecanoic acid; in analogy to the lipase-catalysed esterification reaction of fatty acids with disaccharides (Pedersen et al 2002). Therefore, more ethanoate ester bonds form readily on BC.…”

Section: Thermal Stability Of Bc: Thermo Gravimetry Analysis (Tga)mentioning

confidence: 99%

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Surface only modification of bacterial cellulose nanofibres with organic acids

et al. 2011

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Bacterial cellulose (BC) nanofibres were modified only on their surface using an esterification reaction with acetic acid, hexanoic acid or dodecanoic acid. This reaction rendered the extremely hydrophilic surfaces of BC nanofibres hydrophobic. The hydrophobicity of BC increased with increasing carbon chain length of the organic acids used for the esterification reaction. Streaming (zeta-) potential measurements showed a slight shift in the isoelectric point and a decrease in ζ plateau was also observed after the esterification reactions. This was attributed to the loss of acidic functional groups and increase in hydrophobicity due to esterification of BC with organic acids. A method based on hydrogen/deuterium exchange was developed to evaluate the availability of surface hydroxyl groups of neat and modified BC. The thermal degradation temperature of modified BC sheets decreased with increasing carbon chain length of the organic acids used. This is thought to be a direct result of the esterification reaction, which significantly reduces the packing efficiency of the nanofibres because of a reduction in the number of effective hydrogen bonds between them.

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Section: Xrd Of Neat and Modified Bcmentioning

confidence: 86%

Section: Thermal Stability Of Bc: Thermo Gravimetry Analysis (Tga)mentioning

confidence: 99%

Surface only modification of bacterial cellulose nanofibres with organic acids

et al. 2011

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“…α and β maltose 6'O-acyl esters in an anomeric molar ratio of 1.0:1.1 were synthesized independently of the chain length, but the initial specific reaction rate increased with the chain length, of the acyl donar. The highest initial reaction rate and yield were obtained with the shortest chain length of the acyl donar (Pedersen et al, 2002). The immobilized lipase from C. antarctica was applied to perform the enzymatic esterification of the bioactive compounds with the fatty acids pyridoxine condensate with lauric acid was studied as the model system and lauric acid pyridoxine mono esters with high retention time was obtained as the product.…”

Section: Esterificationmentioning

confidence: 99%

Lipase catalyzed ester synthesis for food processing industries

Rajendran

Palanisamy

Viruthagiri

2009

Braz. arch. biol. technol.

140

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“…Migration of different components took place from the solvent baseline towards the solvent front using a mobile phase which consists of chloroform, methanol, acetic acid and water in a ratio of 35 : 10 : 4 : 1 (v/v) [10]. About 5 ll samples were applied to baseline.…”

Section: Tlc Analysismentioning

confidence: 99%

Enzymatic Synthesis and Characterization of Sucrose Erucate

Jadhav¹,

Pratap²

2017

Tenside Surfactants Detergents

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The enzyme catalyzed synthesis is a environmentally friendly route compared to traditional syntheses. The lipase-catalyzed synthesis of sucrose erucate was achieved in a solvent mixture of t-butanol and dimethyl sulfoxide (4 : 1) by esterification of sucrose with erucic acid using the immobilized Thermomyces lanuginosus lipase. Various process parameters like temperature, substrate molar ratio, solvent, time, and enzyme loading were studied. The optimal conditions for the esterification reaction obtained were 10 %(w/w) enzyme loading, a molar ratio sucrose/fatty acid 1 : 1, mild reaction conditions (50 8C and atmospheric pressure) and reaction time (40 h with 55.6 % conversion). The sugar esters were characterized for surfactant properties at different concentration. Sucrose erucate showed a surface tension of (32.73 ± 0.01) mN m -1 at a critical micellar concentration of 9.8 · 10 -5 mol L -1 and good emulsification power.

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Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides

Cited by 84 publications

References 15 publications

Surface only modification of bacterial cellulose nanofibres with organic acids

Surface only modification of bacterial cellulose nanofibres with organic acids

Lipase catalyzed ester synthesis for food processing industries

Enzymatic Synthesis and Characterization of Sucrose Erucate

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