Enantioselective enzymatic resolution of racemic alcohols by lipases in green organic solvents

Belafriekh, Abderahmane; Secundo, Francesco; Serra, Stefano; Djeghaba, Zeineddine

doi:10.1016/j.tetasy.2017.02.004

Cited by 26 publications

(26 citation statements)

References 52 publications

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“…Moreover,t he coupling efficiency andt he possibility of undesired racemization were also evaluated. The observed behavior was as follows: Scheme5.Assessment of organic solvents in the synthesis of model amides (15)(16)(17)(18)byu sing different coupling agents. [88] Scheme6.Use of CPME as solvent in the peptidesynthesis developedbyJ ad et al [89] ChemSusChem 1 m), but for the other linking reagents solubility was much smaller.…”

Section: Other Emerging Applications Of Cpme In Bioeconomy:c Hromatogmentioning

confidence: 99%

“…[18] The kinetic resolution of (AE)-menthol showedt he highest activity with Candida rugosa lipase (CRL), albeit with low selectivity,a nd CPME proved ag ood solvent for this enzyme. [18] The kinetic resolution of (AE)-menthol showedt he highest activity with Candida rugosa lipase (CRL), albeit with low selectivity,a nd CPME proved ag ood solvent for this enzyme.…”

Section: Introduction:m Otivation For Eco-friendly Solvents and For Cpmementioning

confidence: 99%

“…In an analogous area, the kinetic resolution of structurally different racemic alcohols, such as (AE)-menthol, (AE)-sulcatol, and (AE)-a-cyclogeraniol, was conducted through transesterifications with vinyl acetate and different lipases,w hereby ecofriendly solvents, such as 2-MeTHFa nd CPME, were compared with other classical solvents, such as toluene or methyl tertbutyl ether (MTBE). [18] The kinetic resolution of (AE)-menthol showedt he highest activity with Candida rugosa lipase (CRL), albeit with low selectivity,a nd CPME proved ag ood solvent for this enzyme. Conversely,l ipase AK from Pseudomonas fluorescens led to high selectivity,b ut with low activities and reaction rates, although CPME led to the highest enantioselectivity.…”

Section: Introduction:m Otivation For Eco-friendly Solvents and For Cpmementioning

confidence: 99%

“…In all cases, moderate enantioselectivity was observed independently of the solvent employed with these lipases.T he effect of the lipase formulation for these kinetic resolutions was also studied;t hus, after dissolving it at pH 8.0 and subsequent lyophilization, lipase AK showed highera ctivity in the acetylation of (AE)-menthol in CPME.T his effect was increased when the lyophilization was performed in the presence of additives,such as MeOPEG or sucrose. [18] Therefore, the combination of eco-friendly solvents with an adequate biocatalyst design may enable powerful synergies for synthetic reactions.…”

Section: Introduction:m Otivation For Eco-friendly Solvents and For Cpmementioning

confidence: 99%

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Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Gonzalo

Alcántara

Marı́a³

2019

ChemSusChem

121

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The quest for sustainable solvents is currently a matter of intense research and development, as solvents significantly contribute heavily to the waste generated by chemical industries. Cyclopentyl methyl ether (CPME) is a promising eco‐friendly solvent with valuable properties such as low peroxide formation rate, stability under basic and acidic conditions, and relatively high boiling point. This Review discusses the potential use of CPME for applications in biotechnology (e.g., biotransformations, as solvent or cosolvent), biorefineries, and bioeconomy (e.g., for furan synthesis or as an extractive agent in liquid–liquid separations), as well as for other purposes, such as chromatography or peptide synthesis. Although CPME is currently produced by petrochemical means with a remarkably high atom economy, its biogenic production can be envisaged from substrates such as cyclopentanol or cyclopentanone, which can be derived from furfural or from (bio‐based) adipic acid, respectively. The combination of the promising properties of CPME as a (co)solvent with a future (economic) biogenic origin would be advantageous for setting strategies aligned with the sustainable chemistry principles.

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Section: Other Emerging Applications Of Cpme In Bioeconomy:c Hromatogmentioning

confidence: 99%

Section: Introduction:m Otivation For Eco-friendly Solvents and For Cpmementioning

confidence: 99%

Section: Introduction:m Otivation For Eco-friendly Solvents and For Cpmementioning

confidence: 99%

Section: Introduction:m Otivation For Eco-friendly Solvents and For Cpmementioning

confidence: 99%

See 2 more Smart Citations

Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Gonzalo

Alcántara

Marı́a³

2019

ChemSusChem

121

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“…Unlike the use of chemical catalysts, lipases are considered as key pillar in green chemistry and thus have been widely involved for efficient flavor synthesis also in green organic solvents …”

Section: Introductionmentioning

confidence: 99%

Natural flavor ester synthesis catalyzed by lipases

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Bouzemi

Guo

et al. 2019

Flavour & Fragrance J

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In spite of the fact that several flavors and fragrances are obtained either by chemical synthesis or by extraction from plants, the application of biocatalysis for the sake of a safe and productive pathway by more sustainable chemical processes is the main alternative. The current study focuses on the synthesis of three flavor esters, namely cis‐3‐hexen‐1‐yl acetate, 2‐phenylethyl acetate, and methyl phenylacetate, via transesterification and esterification of the natural corresponding alcohols or acids. The impact of optimizing variables that influence this lipase‐catalyzed synthesis, such as enzyme formulations, solvent‐free media, and acetylating agents, is crucial to achieving higher conversions. The enzymatic transesterification using Novozym 435 afforded cis‐3‐hexen‐1‐yl, and 2‐phenylethyl acetates with high yields (>90%) in green solvents. Similar results were obtained in solvent‐free system, which is more economic for the scaling up of this synthesis. In the case of esterification reactions, the removal of water, formed as a by‐product, with the use of Aquasorb enhanced the conversions as in the case of methyl phenylacetate attained with a conversion of 89% in the presence of Novozym 435. However, this effect was not observed in the larger scale reaction (with 0.85 mol of cis‐3‐hexen‐1‐ol). Instead, the efficient strategy of gradual addition of acetic acid has proven to significantly improve the yield of cis‐3‐hexen‐1‐yl acetate (from 2% up to about 80% in the case of the preparative reaction with 100 mL substrate). Box‐Behnken analysis was also performed to identify the lowest amount of acetylating agent and the shorter time to obtain the highest conversion ratio. This analysis showed that a triacetin/alcohol molar ratio of 1 and 1.75 can be sufficient to obtain a conversion >90% and up to 95%, for cis‐3‐hexen‐1‐yl acetate and 2‐phenylethyl acetate, respectively, similarly to what is obtained with higher triacetin/alcohol molar ratios and comparable reaction time.

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Dynamic Kinetic Resolution for Asymmetric Synthesis

Akai

Moustafa

2019

Kinetic Control in Synthesis and Self-Assembly

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Enantioselective enzymatic resolution of racemic alcohols by lipases in green organic solvents

Cited by 26 publications

References 52 publications

Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Natural flavor ester synthesis catalyzed by lipases

Dynamic Kinetic Resolution for Asymmetric Synthesis

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