The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

Aouf, Chahinez; Durand, Erwann; Lecomte, Jérôme; Figueroa-Espinoza, María-Cruz; Dubreucq, Éric; Fulcrand, Hélène; Villeneuve, Pierre

doi:10.1039/c3gc42143k

Cited by 103 publications

(58 citation statements)

References 150 publications

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“…Owing to the aforementioned operational hazards, the undesired acetic wastes, by-products, and low turnover frequencies compared to biological systems [138], the alternative chemo-enzymatic routes offer significant advantages in terms of selectivity and eco-friendliness. Therefore, they have been researched in the last three decades [9,16,[139][140][141]. In the chemo-enzymatic epoxidation the peroxycarboxylic acid is synthesized directly from carboxylic acid and H 2 O 2 and spontaneously oxidizes the alkene afterward (figure 2.14) [12,13].…”

Section: Chemo-enzymatic Epoxidationmentioning

confidence: 99%

Produktion von Peroxyoktansäure mittels immobilisierter CalB: Realisierbarkeitsstudie im einphasigen Stoffsystem mit graduellem Wasserstoffperoxid‐Dosing

Meyer

Horst

Steinhagen

et al. 2016

Chemie Ingenieur Technik

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Section: Chemo-enzymatic Epoxidationmentioning

confidence: 99%

Produktion von Peroxyoktansäure mittels immobilisierter CalB: Realisierbarkeitsstudie im einphasigen Stoffsystem mit graduellem Wasserstoffperoxid‐Dosing

Meyer

Horst

Steinhagen

et al. 2016

Chemie Ingenieur Technik

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“…[1][2][3][4][5] Polyesters, a type of multifunctional material, are receiving an increasing demand in a multitude of industrial applications. 17,18 The use of modern synthetic techniques, together with enzymatic and microbial methods, has led to an extraordinary expansion of synthetic routes for the production of novel fatty acid compounds, [19][20][21][22] generated from selectively modication in the alkyl chains. Due to decreasingly low availability of fossil resources, bio-based resources represent interesting "green" alternatives to provide the precursors needed for polyester synthesis.…”

Section: Introductionmentioning

confidence: 99%

Polyesters derived from bio-based eugenol and 10-undecenoic acid: synthesis, characterization, and structure–property relationships

Zhao

et al. 2015

RSC Adv.

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Renewable monomers derived from eugenol and 10-undecenoic acid were synthesized via thiol-ene click and nucleophilic substitution reactions. With these monomers in hand, a series of thermoplastic polyesters with tunable thermo-mechanical properties were prepared via two-step melt polycondensation. The prepared polyesters exhibit weight-average molecular weights in the range of 21 000-48 000 g mol À1 , together with polydispersity values between 1.8 and 2.1. Experiments involving thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical analysis (DMA) were carried out in order to study the thermal and mechanical properties of the polymers. All prepared polyester species prove to be thermally stable at temperatures up to 300 C. Furthermore, the aromatic and semi-aromatic polyesters exhibit fully amorphous behaviours with glass transition temperatures (T g s) ranging between À34.13 and 6.97 C. Herein, the density of the rigid aromatic rings along the main chains of the polyester has a distinct influence on the T g values. Furthermore, the fully aliphatic polyesters prove to be semi-crystalline with inconspicuous T g . The incorporation of aromatic eugenol into the polyester chains and the density of the benzene rings were also found to result in a significant improvement in the mechanical properties, including Young's modulus and elongation at break in the range of 11.6 to 44.2 MPa and 33.6-106.7%, respectively. The relatively high tan d and the low storage modulus indicate that eugenol-based polyesters feature superior viscosity properties and may therefore find future applicability in a variety of high-tech materials.

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“…In this context, lipase-based conversions involving abietic acid and complex resinic acids, such as pine/colofony, which are only soluble in trementine oil (Illanes et al 2008;Aouf et al 2014), and hydrolysates of collagen (or other similar substances) and polyols, such as pentaerithritol, which are almost insoluble in all types of solvents, are already a challenging issue. For all of these cases, several strategies have been examined: i) the use of water/solvent biphase systems;…”

Section: Biocatalysis Innovation Guided By Metagenomicsmentioning

confidence: 99%

Biodiversity for biocatalysis: A review of the α/β-hydrolase fold superfamily of esterases-lipases discovered in metagenomes

Ferrer

Bargiela

Martínez-Martínez

et al. 2015

Biocatalysis and Biotransformation

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Natural biodiversity undoubtedly inspires biocatalysis research and innovation.Biotransformations of interest also inspire the search for appropriate biocatalysts in nature.Indeed, natural genetic resources have been found to support the hydrolysis and synthesis of not only common but also unusual synthetic scaffolds. The emerging tool of metagenomics has the advantage of allowing straightforward identification of activity directly applicable as biocatalysis. However, new enzymes must not only have outstanding properties in terms of performance but also other properties superior to those of well-established commercial preparations in order to successfully replace the latter. Esterases (EST) and lipases (LIP) from the α/ -hydrolase fold superfamily are among the enzymes primarily used in biocatalysis. Accordingly, they have been extensively examined with metagenomics. Here we provided an updated (October 2015) overview of sequence and functional datasets of 288 EST-LIP enzymes with validated functions that have been isolated in metagenomes and (mostly partially) characterized. Through sequence, biochemical and reactivity analyses we attempted to understand the phenomenon of variability and versatility within this group of enzymes and to implement this knowledge to identify sequences encoding EST-LIP which may be useful for biocatalysis. We found that the diversity of described EST-LIP polypeptides was not dominated by a particular type of protein or highly similar clusters of proteins but rather by diverse nonredundant sequences. Purified EST-LIP exhibited a wide temperature activity range of 10-85°C, although a preferred bias for a mesophilic temperature range (35-40ºC) was observed. At least 60% of the total characterized metagenomics-derived EST-LIP showed outstanding properties in terms of stability (solvent tolerance) and reactivity (selectivity and substrate profile), which are the features of interest in biocatalysis. We hope that, in the future, the search for and utilization of sequences similar to those already encoded and characterized EST-LIP enzymes 3 from metagenomes may be of interest for promoting unresolved biotransformations in the chemical industry. Some examples are discussed in this review.4

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The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

Cited by 103 publications

References 150 publications

Produktion von Peroxyoktansäure mittels immobilisierter CalB: Realisierbarkeitsstudie im einphasigen Stoffsystem mit graduellem Wasserstoffperoxid‐Dosing

Produktion von Peroxyoktansäure mittels immobilisierter CalB: Realisierbarkeitsstudie im einphasigen Stoffsystem mit graduellem Wasserstoffperoxid‐Dosing

Polyesters derived from bio-based eugenol and 10-undecenoic acid: synthesis, characterization, and structure–property relationships

Biodiversity for biocatalysis: A review of the α/β-hydrolase fold superfamily of esterases-lipases discovered in metagenomes

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