Strategies for the synthesis of fluorinated polyesters

Xin, Zhao; Noro, Jennifer; Fu, Jiajia; Silva, Carla; Cavaco-Paulo, Artur

doi:10.1039/c8ra10341k

Cited by 4 publications

(7 citation statements)

References 27 publications

(41 reference statements)

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“…Highly hydrophobic polyesters were recently synthesized by Zhao et al., [ 38 ] using fluorinated compounds. The produced polymers, poly(ethylene tetrafluorosuccinate), poly(ethylene hexafluoroglutarate), and poly(ethylene octafluoroadipate) were isolated with higher yield when immobilized CALB was used as catalyst.…”

Section: Historical Perspective Of Lipasesmentioning

confidence: 99%

“…The produced polymers, poly(ethylene tetrafluorosuccinate), poly(ethylene hexafluoroglutarate), and poly(ethylene octafluoroadipate) were isolated with higher yield when immobilized CALB was used as catalyst. [ 38 ]…”

Section: Historical Perspective Of Lipasesmentioning

confidence: 99%

“…A similar approach was later performed by Tomke et al, [37] wherein the same polymer was synthesized by the lipase, as well as poly(ethylene malonate) and poly(ethylene phthalate). [37] Highly hydrophobic polyesters were recently synthesized by Zhao et al, [38] using fluorinated compounds. The produced polymers, poly(ethylene tetrafluorosuccinate), poly(ethylene hexafluoroglutarate), and poly(ethylene octafluoroadipate) were isolated with higher yield when immobilized CALB was used as catalyst.…”

Section: Textile/polymer Applicationsmentioning

confidence: 99%

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Chemical modification of lipases: A powerful tool for activity improvement

Noro

Cavaco‐Paulo

Silva

2022

Biotechnology Journal

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The demand for adequate and ecologically acceptable procedures to produce the most differentiated products has been growing in recent decades, with enzymes being excellent examples of the advances achieved so far. Lipases are astonishing catalysts with a vast range of applications including the synthesis of esters, flavors, biodiesel, and polymers. The broad specificity of the substrates, as well as the regio-, stereo-, and enantioselectivity, are the differentiating factors of these enzymes. Structural modification is a current approach to enhance the activity of lipases. Chemical modification of lipases to improve catalytic performance is of great interest considering the increasingly broad fields of application. Together with the physical immobilization onto solid supports, different strategies have been developed to produce catalysts with higher activity and stability. In this review, practical insights into the different strategies developed in recent years regarding the modification of lipases are described. For the first time, the impact of the modifications on the activity and stability of lipases, as well as on the biotechnological applications, is fully compiled.

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Section: Historical Perspective Of Lipasesmentioning

confidence: 99%

Section: Historical Perspective Of Lipasesmentioning

confidence: 99%

Section: Textile/polymer Applicationsmentioning

confidence: 99%

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Chemical modification of lipases: A powerful tool for activity improvement

Noro

Cavaco‐Paulo

Silva

2022

Biotechnology Journal

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“…7A ). Likewise, many other types of fluorinated compounds were also obtained by lipases, like 2,2,2-trifluoroethyl trifluoromethyl sulfate, fluorinated polyesters, and meso -2,4,6-trifluoro-1,3,5,7-tetrahydroxyheptane-1,7-diacetate (Bentler et al 2019 ; Snoch et al 2019 ; Zhao et al 2019b ). Importantly, lipase has good resistance to organic solvents in addition to being able to catalyze cheap ester substrates.…”

Section: Enzymatic Synthesis Of Fluorinated Compoundsmentioning

confidence: 99%

Enzymatic synthesis of fluorinated compounds

Cheng

2021

Appl Microbiol Biotechnol

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Fluorinated compounds are widely used in the fields of molecular imaging, pharmaceuticals, and materials. Fluorinated natural products in nature are rare, and the introduction of fluorine atoms into organic compound molecules can give these compounds new functions and make them have better performance. Therefore, the synthesis of fluorides has attracted more and more attention from biologists and chemists. Even so, achieving selective fluorination is still a huge challenge under mild conditions. In this review, the research progress of enzymatic synthesis of fluorinated compounds is summarized since 2015, including cytochrome P450 enzymes, aldolases, fluoroacetyl coenzyme A thioesterases, lipases, transaminases, reductive aminases, purine nucleoside phosphorylases, polyketide synthases, fluoroacetate dehalogenases, tyrosine phenol-lyases, glycosidases, fluorinases, and multienzyme system. Of all enzyme-catalyzed synthesis methods, the direct formation of the C-F bond by fluorinase is the most effective and promising method. The structure and catalytic mechanism of fluorinase are introduced to understand fluorobiochemistry. Furthermore, the distribution, applications, and future development trends of fluorinated compounds are also outlined. Hopefully, this review will help researchers to understand the significance of enzymatic methods for the synthesis of fluorinated compounds and find or create excellent fluoride synthase in future research. Key points • Fluorinated compounds are distributed in plants and microorganisms, and are used in imaging, medicine, materials science . • Enzyme catalysis is essential for the synthesis of fluorinated compounds . • The loop structure of fluorinase is the key to forming the C-F bond . Supplementary Information The online version contains supplementary material available at 10.1007/s00253-021-11608-0.

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“…The combi-lipases of pRML and MDL can effectively improve the hydrolysis rate of lard to 78.1%, but the remaining 21.9% of lard should be addressed. Studies have found that ultrasound is a promising method for enzymatic synthesis [31,32]. Ultrasound pretreatment promoted diacylglycerol production from lard through lipasecatalyzed glycerolysis and does not change the structure of lard [19].…”

Section: Ultrasound Pretreatment Accelerates Reaction Rate and Improves Hydrolysis Efficiencymentioning

confidence: 99%

Ultrasound-assisted hydrolysis of lard for free fatty acids catalyzed by combined two lipases in aqueous medium

Huang

Zhao

et al. 2020

Bioengineered

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Lard is a by-product of animal processing. It is inexpensive compared with vegetable oils; however, its use is limited due to the high calorific value and high-saturated fatty acid content. While using lard as the source of free fatty acids (FFA) can significantly increase its utilization value. This study aimed to research the method on efficient hydrolysis of lard catalyzed by combi -lipases and assisted with ultrasound pretreatment. A 1,3-specific lipase from Rhizomucor miehei (termed pRML, 1540 U/mL) and a nonspecific mono- and diacylglycerol lipase from Penicillium cyclopium (termed MDL, 2000 U/mL) were used as biocatalysts. Results showed that the maximum hydrolysis rate of lard after 6 h at 45°C by using pRML and MDL alone was, respectively, 39.9% and 8.5%. When pRML combined with MDL ( combi -lipases), hydrolysis rate can reach to 78.1%. While combi -lipases were assisted with 5 min ultrasound pretreatment before the reaction, the hydrolysis rate can further increase to 97%. The combi -lipases with different specificity and assisted with ultrasound pretreatment may be a useful technology for the enzyme production of FFA from complex lipid substrates, such as lard.

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Strategies for the synthesis of fluorinated polyesters

Abstract: In this work we synthetized three fluorinated polyesters from dimethyl tetrafluorosuccinate (DMTFS), dimethyl hexafluoroglutarate (DMHFG), and dimethyl octafluoroadipate (DMOFA) and ethylene glycol.

Cited by 4 publications

References 27 publications

Chemical modification of lipases: A powerful tool for activity improvement

Chemical modification of lipases: A powerful tool for activity improvement

Enzymatic synthesis of fluorinated compounds

Ultrasound-assisted hydrolysis of lard for free fatty acids catalyzed by combined two lipases in aqueous medium

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