含苯丙氨酸甲酯侧链螺旋聚苯异腈的合成与性能研究  

Synthesis and Properties of Helical Poly(phenyl isocyanide)with Methyl Phenylalanine on the Side Chain

作　　者：张达 郭雅润 潘乐园 周俊杰 黄胜堂[1] 吴诗[1] 郭丽媛[1] ZHANG Da;GUO Ya-run;GUO Li-yuan(School of Pharmacy,Xianning Medical College,Hubei University of Science and Technology,Xianning Hubei 437100,China)

机构地区：[1]湖北科技学院医学部药学院,湖北咸宁437100

出　　处：《湖北科技学院学报（医学版）》2024年第6期488-492,共5页Journal of Hubei University of Science and Technology(Medical Sciences)

基　　金：湖北科技学院2023年度医学科研专项基金资助(2023YKY02):国家级科研项目培育计划项目(2022-24GP03);湖北省大学生创新创业项目(S202010927036)。

摘　　要：目的设计合成一个含有苯丙氨酸甲酯侧链的螺旋聚苯异腈,为螺旋结构在药物递送系统提供一个新材料。方法以苯丙氨酸为起始原料,甲酯后与对甲酰氨基苯甲酸缩合,再脱水得到含有L/D-苯丙氨酸甲酯侧链的苯异腈单体,通过1,3-双(二苯基膦丙烷)二氯化镍[Ni(dppp)Cl 2]催化聚合反应获得一对具有螺旋性的聚苯异腈化合物Poly-L/D-PhePI。结果单体和聚合物结构经NMR、IR表征确定,GPC测定其分子量为M n=8.9kDa,M w/M n=2.41;聚合物的比旋光度是单体的10倍以上,聚合物的Poly-L/D-PhePI的CD呈现良好的Cotton效应与对称性。结论成功合成含有丙氨酸甲酯侧链的螺旋聚苯异腈,为新型给药系统方面提供物质基础。Objective To design and synthesize a helical poly(phenyl isocyanide)with methyl phenylalanine on the side chain,in order to provide a kind of new material for helical structure used in drug delivery system.Methods We first used phenylalanine as the starting material for methyl esterification,and condensated with p-formylaminobenzoic acid,and then synthesized a group of phenyl isocyanide monomers containing L/D-phenylalanine groups,and finally obtained a pair of chiral helical poly-L/D-PhePI compounds by catalytic polymerization of 1,3-bis(diphenylphosphopropane)nickel dichloride[Ni(dppp)Cl 2].Results The structure of Poly-L/D-PhePI was characterized by NMR and IR,and its polymerization degree was determined by GPC to be Mn=8.9 kDa and M w/M n=2.41 kDa.The specific Optical Rotation of the polymer is more than 10 times that of the monomer.The CD spectrum of the polymers shows strong and opposite Cotton effects.Conclusion We successfully synthesize a helical polyphenylene isonitrile containing alanine methyl ester side chain,which will provides a new way to be designed for new drug delivery system.

关 键 词：苯丙氨酸 螺旋聚合物 聚苯异腈 药物递送系统 

分 类 号：R944[医药卫生—药剂学]