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

作　　者：Jingsong Yuan Dong Shi Yi Zhang Jianhua Lu Letian Wang Er-Qiang Chen Hua Lu 

机构地区：[1]Beijing National Laboratory for Molecular Sciences,Center for Soft Matter Science and Engineering,Key Laboratory of Polymer Chemistry and Physics of Ministry of Education,College of Chemistry and Molecular Engineering,Peking University,Beijing 100871(China)

出　　处：《CCS Chemistry》2020年第5期236-244,共9页中国化学会会刊（英文）

基　　金：National Natural Science Foundation of China(21722401 for H.Lu and 21634001 for E.Q.Chen).

摘　　要：Degradable polyesters have long been regarded as eco-friendly materials,useful for various applicationswhile meeting the growing needs of sustainability.However,it is still challenging to synthesize functional aliphatic polyesters from abundant and cheap renewable sources.Our 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 derivatization.The 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 epimerization.This process afforded stereoregular polyesters PNRPE with molar mass(M_(n))up to 90 kg/mol and a narrow dispersity(Ð)generally below 1.10.The 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 polyesters.The utility of the polymers was showcased by the facile site-specific bioconjugation of PN^(EG3)PE,a water-soluble polyester,to a protein.This 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 

分 类 号：O62[理学—有机化学]