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Sustainable Polyamides Enabled by Controlled Ring-opening Polymerization of 4-hydroxyproline-derived Lactams

Chinese Journal of Polymer Science 2023年第5期41卷 728-734,I0008页

作者： Jian-Qun Wang Xian-Hong Wang You-Hua Tao Key Laboratory of Polymer Ecomaterials Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China University of Science and Technology of China Hefei 230026China

Aliphatic polyamides have been considered as eco-friendly materials,useful for a wide range of ***,it still presents obstacle to produce sustainable aliphatic polyamides from abundant renewable ***,we describe that 4-hydroxyproline(4-HYP),a renewable resource,was readily converted to its corresponding bicyclic bridged lactam monomers bearing pendant Boc-protected secondary amino group,and oligo-ethylene glycol *** hexamethyldisilazide(LiHMDS)-mediated polymerization of the resulting monomers exhibited a controlled feature,affording sustainable aliphatic polyamides with number-average molecular weight up to 73 kg/mol and a low molecular weight distribution?<***,this work can lead to a novel kind of functional and sustainable polyamides with potential applications,including degradable plastics,and drug delivery.

关键词： Polyamides Renewable Ring-opening polymerization 4-hydroxyproline

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Synthesis and Characterization of a Novel Functional Biodegradable Copolymer-Poly(lactic acid-4-hydroxyproline-polyethylene glycol)

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Chinese Chemical Letters 2006年第8期17卷 1125-1128页

作者： Jiu Fang DUAN Yu Bin ZHENG Department of Polymer Science Dalian University of Technology Dalian 116012

A series of poly（lactic acid-4-hydroxyproline-polyethylene glycol）（PLA-Hpr-PEG） copolymers were synthesized by direct melt copolymerization of D,L-lactic acid and 4-hydroxyproline with different feed amount of polyethylene glycol （PEG） 0.1%, 0.5%, 1% and 5%, respectively. The properties of these copolymers were characterized by using IR spectroscopy, proton nuclear magnetic resonance （1H-NMR） spectroscopy, gel permeation chromatography （GPC）, X-ray diffraction and differential scaning calorimetry （DSC）. PLA-Hpr-PEG are amorphous copolymers. Copolymers showed increasing water uptake capacity with increasing PEG percentage in the feed, which result in an increasing degradable rate in phosphate buffer solution （pH 7.4） at 37℃.

关键词： Lactic acid 4-hydroxyproline polyethylene glycol.

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4-Hydroxy-L-Proline as a General Platform for Stereoregular Aliphatic Polyesters:Controlled Ring-Opening Polymerization,Facile Functionalization,and Site-Specific Bioconjugation

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CCS Chemistry 2020年第5期2卷 236-244页

作者： Jingsong Yuan Dong Shi Yi Zhang Jianhua Lu Letian Wang Er-Qiang Chen Hua Lu Beijing National Laboratory for Molecular Sciences Center for Soft Matter Science and EngineeringKey Laboratory of Polymer Chemistry and Physics of Ministry of EducationCollege of Chemistry and Molecular EngineeringPeking UniversityBeijing 100871(China)

Degradable polyesters have long been regarded as eco-friendly materials,useful for various applicationswhile meeting the growing needs of ***,it is still challenging to synthesize functional aliphatic polyesters from abundant and cheap renewable *** present study reports a readily available and versatile platform for producing functional and stereoregular aliphatic polyesters from 4-hydroxy-L-proline(4-HYP).We synthesized a bicyclic bridged lactone monomer,namely,NR-PL,by a simple and scalable two-step process allowing facile side-chain functionalization and *** ring-opening homopolymerization and copolymerization for the generation of N^(R)-PL were controlled fully by using organobases such as 1,8-diazabicyclo[5.4.0]-undec-7-ene(DBU)without any detectable *** process afforded stereoregular polyesters PNRPE with molar mass(M_(n))up to 90 kg/mol and a narrow dispersity(Ð)generally below *** uniqueness of the backbone,which contains two chiral centers on a rigid propyl ring,together with the versatility of the side chain,offer tunable properties complementary to existing aliphatic *** utility of the polymers was showcased by the facile site-specific bioconjugation of PN^(EG3)PE,a water-soluble polyester,to a *** work might open numerous opportunities in creating functional and sustainable polyesters for a wide range of applications,including degradable plastics,drug delivery,and protein therapeutics.

关键词： 4-hydroxyproline ROP sustainable polyester stereoregular bioconjugation

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