手性温敏凝胶Poly(NIPAM-co-AAc-L-Trp)的制备及性能  

SYNTHESIS AND CHIRAL RECOGNITION PROPERTY OF THERMO-SENSITIVE POLY( NIPAM-co-AAC-L-TRP) HYDROGELS

作　　者：陈娇娇[1] 侯蔺桐[2] 陈莉[2] 张艳玲[1] 

机构地区：[1]天津工业大学环境与化学工程学院,天津300387 [2]天津工业大学材料科学与工程学院,天津300387

出　　处：《高分子学报》2013年第11期1412-1418,共7页Acta Polymerica Sinica

基　　金：国家自然科学基金(基金号20904039);天津市应用基础及前沿技术研究计划(项目号10JCYBJC02900);天津市自然科学基金重点项目(基金号10JCZDJC21900)资助

摘　　要：利用L-色氨酸(L-Trp)为手性源,经酯化、缩合等反应制备手性单体AAc-L-Trp,进而在交联剂N,N'-亚甲基双丙烯酰胺(MBAA)和引发剂偶氮二异丁腈(AIBN)的作用下,与N-异丙基丙烯酰胺(NIPAM)发生自由基共聚制备了一种可用于手性拆分的新型手性温敏水凝胶Poly(NIPAM-co-AAc-L-Trp),其结构经IR确证.通过对其温敏性研究发现,相比于PNIPAM凝胶,疏水性手性单体的引入使Poly(NIPAM-co-AAc-L-Trp)凝胶的温敏性下降,LCST随着手性单体含量的增加而降低.以DL-苯丙氨酸为模型药物对其手性识别和拆分性能进行研究,结果表明,手性温敏凝胶可选择性地吸附D-型对映体,且吸附量随着手性单体含量增加而增加;提高温度(45°C)有利于手性温敏凝胶对DL-苯丙氨酸的拆分.Thermo-sensitive hydrogels based on N-isopropylacrylamide （NIPAM） containing L-amino acid groups were designed and synthesized for chiral resolution.L-tryptophane was used as chiral pool,after esterifization and condensation reactions with acryloyl chloride and the chiral monomer AAc-L-Trp was obtained,and the structure was characterized by IR and 1H-NMR.Then the subsequent copolymerization was carried on between AAc-L-Trp and NIPAM with N,N＇-methylenebisacrylamide （MBAA） as linkage agent in the presence of azobisisobutyronitrile （AIBN） in ethanol with different weight ratios.The resulted poly-（NIPAM-co-AAc-L-Trp） hydrogels were identified by IR.The swelling behaviors,deswelling and reswelling kinetics of the chiral hydrogels have been studied,and the results showed that all the poly（NIPAM-co-AAc-L-Trp） hydrogels exhibited evident temperature-sensitivity.Due to the hydrophobicity of chiral monomer incorporated into the structure of the chiral gels,the thermo-sensitivity of the chiral gels is lower than that of PNIPAM gel,and the lower critical solution temperature （LCST） decreased with increasing of the contents of chiral monomer.The chiral adsorption and separation performance were also investigated using D/L-phenylalanine （D/L-Phe） as a model.The results indicated that compared with PNIPAM gel,the chiral gels performed higher adsorption rate and larger adsorption quantities for D-Phe enantiomers.Increasing the contents of chiral monomer or the temperature will improve the efficiency of resolution of DL-Phe.

关 键 词：温敏凝胶 N-异丙基丙烯酰胺 L-色氨酸 合成 手性识别 

分 类 号：O631.3[理学—高分子化学]