Stereoselectivity-tailored chemo-enzymatic synthesis of enantiocomplementary poly (ω-substituted-δ-valerolactone) enabled by engineered lipase

Zhu, Qiaoyan; Fei, Zhengdong; Lin, Xianfu; Xia, Bo; Wu, Qi

doi:10.1016/j.eurpolymj.2019.07.006

Cited by 7 publications

(1 citation statement)

References 45 publications

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“…The key stage of this methodology was the acylation of racemic substituted homoallylic alcohols followed by stereoselective hydrolysis catalyzed by wild and mutant forms of lipase B from Candida antarctica . Different lactone monomers were obtained in six stages, one being biocatalytic and leading to the enantiomeric excess of stereoselective hydrolyses 90–99% with a conversion of 42–99% [ 260 ].…”

Section: Biocatalytic Production Of Monomersmentioning

confidence: 99%

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Nikulin

Švedas

2021

Molecules

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Trends in the dynamically developing application of biocatalysis for the synthesis and modification of polymers over the past 5 years are considered, with an emphasis on the production of biodegradable, biocompatible and functional polymeric materials oriented to medical applications. The possibilities of using enzymes not only as catalysts for polymerization but also for the preparation of monomers for polymerization or oligomers for block copolymerization are considered. Special attention is paid to the prospects and existing limitations of biocatalytic production of new synthetic biopolymers based on natural compounds and monomers from biomass, which can lead to a huge variety of functional biomaterials. The existing experience and perspectives for the integration of bio- and chemocatalysis in this area are discussed.

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Section: Biocatalytic Production Of Monomersmentioning

confidence: 99%

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Nikulin

Švedas

2021

Molecules

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Enantiodivergent Chemoenzymatic Dynamic Kinetic Resolution: Conversion of Racemic Propargyl Alcohols into Both Enantiomers

Horino

Nishio

Kawanishi

et al. 2022

Chemistry A European J

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Natural lipases typically recognize enantiomers of alcohols based on the size differences of substituents near the carbinol moiety and selectively react with the R enantiomers of secondary alcohols. Therefore, lipase-catalyzed dynamic kinetic resolution (DKR) of racemic secondary alcohols produces only R enantiomers. We report herein a method for obtaining S enantiomers by DKR of secondary 3-(trialkylsilyl)propargyl alcohols by using a well-known Rselective Pseudomonas fluorescens lipase in combination with a racemization catalyst VMPS4, in which the silyl group reverses the size relationship of substituents near the carbinol moiety. We have already reported R-selective DKR of the corresponding propargyl alcohols without substituents on the ethynyl terminal carbon, and the presence of an easily removable silyl group has enabled us to produce both enantiomers of propargyl alcohols in high chemical yields and with high enantiomeric excess. In addition, immobilization of the lipase on Celite was found to be important for achieving a high efficiency of the DKR.

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Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

Hevilla

Sonseca

Echeverría

et al. 2021

Macromolecular Bioscience

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This article reviews the most important advances in the enzymatic synthesis of polyesters. In first place, the different processes of polyester enzymatic synthesis, i.e., polycondensation, ring opening, and chemoenzymatic polymerizations, and the key parameters affecting these reactions, such as enzyme, concentration, solvent, or temperature, are analyzed. Then, the latest articles on the preparation of polyesters either by direct synthesis or via modification are commented. Finally, the main bioapplications of enzymatically obtained polyesters, i.e., antimicrobial, drug delivery, or tissue engineering, are described. It is intended to point out the great advantages that enzymatic polymerization present to obtain polymers and the disadvantages found to develop applied materials.

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Stereoselectivity-tailored chemo-enzymatic synthesis of enantiocomplementary poly (ω-substituted-δ-valerolactone) enabled by engineered lipase

Cited by 7 publications

References 45 publications

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Prospects of Using Biocatalysis for the Synthesis and Modification of Polymers

Enantiodivergent Chemoenzymatic Dynamic Kinetic Resolution: Conversion of Racemic Propargyl Alcohols into Both Enantiomers

Enzymatic Synthesis of Polyesters and Their Bioapplications: Recent Advances and Perspectives

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