New chemosynthetic route to linear ε-poly-lysine

Tao, Youhua; Chen, Xiaoyu; Jia, Fan; Wang, Shixue; Xiao, Chunsheng; Cui, Fengchao; Li, Yunqi; Bian, Zheng; Chen, Xuesi; Wang, Xianhong

doi:10.1039/c5sc02479j

Cited by 58 publications

(61 citation statements)

References 50 publications

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“…Our group has reported the cyclization reaction of biorenewable lysine for the synthesis of α‐amino‐ε‐caprolactam . Here, ACL monomer was prepared by amidation of α‐amino‐ε‐caprolactam with acryloyl chloride, in modest yields [Figure (B)].…”

Section: Resultsmentioning

confidence: 99%

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Controlled synthesis of thermoresponsive polymers derived from l‐Lysine, a biorenewable resource

Liu

Luo

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Renewable lysine was cyclized to its corresponding α‐amino‐ε‐caprolactam and then underwent the reaction with acryloyl chloride to harvest a 2‐acrylamido‐caprolactam (ACL) monomer. Subsequent reversible addition–fragmentation chain transfer copolymerization of the obtained monomer with oligo(ethylene glycol)acrylate (OEGA) gave well‐defined P(ACL‐co‐OEGA) with low distribution. Nuclear magnetic resonance , size exclusion chromatography, and matrix‐assisted laser desorption ionization–time‐of‐flight–mass spectrometry measurements indicated the controlled feature of the polymerization. Moreover, the resultant copolymers demonstrated thermoresponsiveness, and the cloud points (Tcp) can be adjusted from 34 to 79 °C, by changing pH values, and the fraction of cyclic lysine. These results suggested that these lysine‐based thermoresponsive polymers might be used as new materials in biomedical fields. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 862–868

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Section: Resultsmentioning

confidence: 99%

“…l ‐Lysine is becoming an ideal synthetic feedstock as it is renewable, abundant, and inexpensive . Here, we assumed that the preparation of cyclization of lysine, followed by the reaction with acryloyl chloride could result in polymerizable 2‐acrylamido‐caprolactam (ACL) monomer [Fig.…”

Section: Introductionmentioning

confidence: 99%

Controlled synthesis of thermoresponsive polymers derived from l‐Lysine, a biorenewable resource

Liu

Luo

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…Compared with chemical method, which requires repetitive protection/ deprotection reactions and/or many chemical compounds, microorganisms are more practical, efficient, and environment friendly for ɛ-PL production (Kushwaha et al 1980;Tao et al 2015). Microbial ɛ-PL was first discovered in 1977, when Shima and Sakai screened Dragendorffpositive compounds (Shima and Sakai 1977).…”

Section: Introductionmentioning

confidence: 99%

Recent advances in the biotechnological production of microbial poly(ɛ-l-lysine) and understanding of its biosynthetic mechanism

Feng

et al. 2016

Appl Microbiol Biotechnol

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Poly(ɛ-L-lysine) (ɛ-PL) is an unusual biopolymer composed of L-lysine connected between α-carboxyl and ɛ-amino groups. It has been used as a preservative in food and cosmetics industries, drug carrier in medicines, and gene carrier in gene therapy. Modern biotechnology has significantly improved the synthetic efficiency of this novel homopoly(amino acid) on an industrial scale and has expanded its industrial applications. In the latest years, studies have focused on the biotechnological production and understanding the biosynthetic mechanism of microbial ɛ-PL. Herein, this review focuses on the current trends and future perspectives of microbial ɛ-PL. Information on the screening of ɛ-PL-producing strains, fermentative production of ɛ-PL, breeding of high-ɛ-PL-producing strains, genomic data of ɛ-PL-producing strains, biosynthetic mechanism of microbial ɛ-PL, and the control of molecular weight of microbial ɛ-PL is included. This review will contribute to the development of this novel homopoly(amino acid) and serve as a basis of studies on other biopolymers.

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“…Amino acids are naturally available renewable resources, and recent advances in aerobic fermentation have made it possible to obtain amino‐acids with high purity and relatively low price. Therefore, extensive research has focused on the synthesis of biorenewable polymers based on amino‐acids monomers . We previously proposed a new chemical strategy based on ring‐opening polymerization (ROP) to obtain ε ‐poly‐lysine from lysine .…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, extensive research has focused on the synthesis of biorenewable polymers based on amino‐acids monomers . We previously proposed a new chemical strategy based on ring‐opening polymerization (ROP) to obtain ε ‐poly‐lysine from lysine . Meanwhile, we have also been investigating controlled ROP of O ‐carboxyanhydride (OCA) monomer obtained from L ‐lysine to generate renewable lysine‐based polyester .…”

Section: Introductionmentioning

confidence: 99%

Precision synthesis of sustainable thermoplastic elastomers from lysine‐derived monomers

Liu

Zhang

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Novel renewable thermoplastic elastomers were synthesized by sequential polymerization of lysine‐ and itaconic acid‐derived monomers. Ring‐opening polymerization of lysine‐based O‐carboxyanhydride monomer using diethylene glycol as an initiator gave well‐defined α,ω‐dihydroxy functionalized lysine‐derived polyesters. The Mn of these polyesters increased with the monomer conversion while retaining relatively narrow molecular weight distributions. Based on the successful controlled polymerization and esterification of α,ω‐dihydroxy with 2‐bromoisobutyryl bromide, the resultant Br‐PL‐Br macroinitiator was used for the atom transfer radical polymerization of N‐phenylitaconimide (PhII). Three poly(N‐phenylitaconimide)‐b‐polyester‐b‐poly(N‐phenylitaconimide) triblock copolymers were prepared containing 12 − 25 mol% PPhII, as determined by 1H NMR spectroscopy. The properties of the obtained triblock copolymer are evaluated as high‐performance and renewable thermoplastic elastomer materials. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 349–355

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New chemosynthetic route to linear ε-poly-lysine

Abstract: ε-poly-lysine (ε-PL) is a naturally-occurring homopolymer produced by the fermentation process. Here, we report a new chemical strategy based on ring opening polymerization to obtain ε-PL from lysine.

Cited by 58 publications

References 50 publications

Controlled synthesis of thermoresponsive polymers derived from l‐Lysine, a biorenewable resource

Controlled synthesis of thermoresponsive polymers derived from l‐Lysine, a biorenewable resource

Recent advances in the biotechnological production of microbial poly(ɛ-l-lysine) and understanding of its biosynthetic mechanism

Precision synthesis of sustainable thermoplastic elastomers from lysine‐derived monomers

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