Reviewing research on the synthesis of CALB-catalyzed sugar esters incorporating systematic mapping principles

Gonçalves, Maria Carolina Pereira; Romanelli, João Paulo; Guimarães, José Renato; Vieira, Ana Carolina; Azevedo, Bruna Pereira de; Tardioli, Paulo Waldir

doi:10.1080/07388551.2021.1888071

Cited by 19 publications

(20 citation statements)

References 104 publications

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“…The use of such enzymes as catalysts in the free form presents some issues related to the instability of their structures and the difficulty of recovery and reuse at the end of the process [ 22 ]. To minimize these drawbacks, CALB immobilization was addressed in about 95% of the publications that encompass the synthesis of SFAEs (in the time span from 2010 to 2019) [ 23 ]. The interfacial adsorption of lipases on hydrophobic supports [ 24 ], covalent bonds, and ionic interactions are among the immobilization techniques reported in this period [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

“…Specifically, the use of the commercial CALB physically adsorbed on a macroporous resin (Novozym 435 and Lipozyme 435) was reported in about 80% of the publications on the synthesis of sugar esters over the last decade [ 23 ]. Novozym 435 and Lipozyme 435 are CALB immobilized on Lewatit VP OC 1600, a poly methacrylic acid cross-linked with divinylbenzene.…”

Section: Introductionmentioning

confidence: 99%

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Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

et al. 2021

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In this paper, we have performed the Lipozyme 435-catalyzed synthesis of xylose oleate in methyl ethyl ketone (MEK) from xylose and oleic acid. The effects of substrates’ molar ratios, reaction temperature, reaction time on esterification rates, and Lipozyme 435 reuse were studied. Results showed that an excess of oleic acid (xylose: oleic acid molar ratio of 1:5) significantly favored the reaction, yielding 98% of xylose conversion and 31% oleic acid conversion after 24 h-reaction (mainly to xylose mono- and dioleate, as confirmed by mass spectrometry). The highest Lipozyme 435 activities occurred between 55 and 70 °C. The predicted Ping Pong Bi Bi kinetic model fitted very well to the experimental data and there was no evidence of inhibitions in the range assessed. The reaction product was purified and presented an emulsion capacity close to that of a commercial sugar ester detergent. Finally, the repeated use of Lipozyme 435 showed a reduction in the reaction yields (by 48 and 19% in the xylose and oleic acid conversions, respectively), after ten 12 h-cycles.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

et al. 2021

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“…Conversely, the A H of the PEI-coated preparation did not decrease after the same process, indicating that the N435 PEI-coating reduced the desorption that has otherwise been reported when using the uncoated biocatalyst. 16,29,40,53,[63][64][65] In a previous study, by the end of five 6 h cycles of xylose laurate synthesis, the A H of the uncoated N435 presented a reduction twofold higher than the A H of the PEI-coated derivative after the biocatalysts' incubation in the crude reaction product. 30 Results from both studies have confirmed that the addition of the PEI layer to the N435 surface reduced enzyme leakage and therefore improved N435 operational stability, facilitating its industrial implementation.…”

Section: N435 Operational Stability In the Synthesis Of Sugar Fatty A...mentioning

confidence: 82%

“…Sugar fatty acid esters are non-ionic surfactants, [24][25][26] synthesized through an esterification reaction between a sugar moiety and a fatty acid, 27 where the sugar acts as the acceptor for an acyl group, while the free fatty acid (FFA) or vinyl ester of fatty acid is the donor of the acyl group. 13,28 Gonçalves et al 29 showed that FFAs were used in 63% of the studies that performed the Candida antarctica lipase B (CALB)-catalyzed synthesis of sugar esters, with lauric, palmitic, and oleic acids accounting for nearly 43% of the occurrences. By using FFAs instead of activated acyl donors (e.g.…”

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confidence: 99%

“…34 The commercial CALB Novozyme 435 (N435) was reported in ~80% of the scientific publications investigating the synthesis of SFAEs from 2010 to 2019. 29 N435 is a CALB immobilized by non-covalent linkage and interfacial activation on Lewatit VP OC 1600, a poly-methacrylic acid crosslinked with divinylbenzene. 35 Despite the extensive use of this enzyme preparation, it is difficult to use it multiple times because of enzyme leaching from the support in the presence of substrates/products with surfactant properties.…”

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confidence: 99%

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Production of sugars from mixed hardwoods for use in the synthesis of sugar fatty acid esters catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B

Gonçalves

Cansian

Tardioli

et al. 2023

Biofuels Bioprod Bioref

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The synthesis of sugar fatty acid esters (SFAEs) from lignocellulosic biomass and oleic acid (C18:1) was catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B in a methyl ethyl ketone medium. After steam‐explosion pretreatment of mixed hardwoods and enzymatic hydrolysis at 15%wt solids, xylose and glucose were purified/concentrated to a mass ratio of ~3 to 1. These lignocellulosic sugars were superior to commercial sugars as the carbohydrate source for the esterification reaction in terms of sugar conversions. The highest conversions were obtained using 1.5% w/v of Novozyme 435 (N435, uncoated) as the biocatalyst for the synthesis of SFAEs. Coating the N435 with polyethyleneimine (PEI) prevented enzyme leakage into the reaction medium and produced 35% and 50% higher xylose and glucose conversions to SFAEs, respectively, at the same enzyme loading. After six 24 h reuse cycles with the PEI‐coated N435, xylose conversion decreased by 44%, while a 65% reduction in xylose conversion was observed with the uncoated lipase. Mass spectrometry analysis confirmed the production of xylose and glucose mono‐ and di‐esters. Our purified product presented an emulsion capacity (EC) close to that of a commercial sugar ester and the ECs of the xylose oleate, laurate, and palmitate synthesized in previous studies.

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From Lactose to Alkyl Galactoside Fatty Acid Esters as Non‐Ionic Biosurfactants: A Two‐Step Enzymatic Approach to Cheese Whey Valorization

et al. 2023

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A library of alkyl galactosides was synthesized to provide the “polar head” of sugar fatty acid esters to be tested as non‐ionic surfactants. The enzymatic transglycosylation of lactose resulted in alkyl β‐D‐galactopyranosides, whereas the Fischer glycosylation of galactose afforded isomeric mixtures of α‐ and β‐galactopyranosides and α‐ and β‐galactofuranosides. n‐Butyl galactosides from either routes were enzymatically esterified with palmitic acid, used as the fatty acid “tail” of the surfactant, giving the corresponding n‐butyl 6‐O‐palmitoyl‐galactosides. Measurements of interfacial tension and emulsifying properties of n‐butyl 6‐O‐palmitoyl‐galactosides revealed that the esters of galactopyranosides are superior to those of galactofuranosides, and that the enantiopure n‐butyl 6‐O‐palmitoyl‐β‐D‐galactoside, prepared by the fully enzymatic route, leads to the most stable emulsion. These results pave the way to the use of lactose‐rich cheese whey as raw material for the obtainment of bio‐based surfactants.

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Reviewing research on the synthesis of CALB-catalyzed sugar esters incorporating systematic mapping principles

Cited by 19 publications

References 104 publications

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

Lipozyme 435-Mediated Synthesis of Xylose Oleate in Methyl Ethyl Ketone

Production of sugars from mixed hardwoods for use in the synthesis of sugar fatty acid esters catalyzed by immobilized‐stabilized derivatives of Candida antarctica lipase B

From Lactose to Alkyl Galactoside Fatty Acid Esters as Non‐Ionic Biosurfactants: A Two‐Step Enzymatic Approach to Cheese Whey Valorization

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