新型富勒烯α-氨基酸的合成及其纳米颗粒水悬液的制备  

Synthesis of Novel Fullerene α-Amino Acids and Preparation of Their Aqueous Nanoparticle Suspensions

作　　者：张静[1] 王艳霞[1] 康峰[1] 彭琦云[1] 杨新林[1] 

机构地区：[1]北京理工大学生命科学与技术学院,北京100081

出　　处：《高等学校化学学报》2008年第10期1986-1989,共4页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20672012)资助

摘　　要：通过1,3-偶极环加成反应合成中间体N-取代的3,4-富勒烯吡咯烷,利用α-氨基与α-羧基均被保护的天冬氨酸或谷氨酸的非α-羧基与中间体N-取代的3,4-富勒烯吡咯烷衍生物的活化羟基进行缩合反应,产物脱保护后得到了2种新的α-富勒烯氨基酸:富勒烯天冬氨酸和富勒烯谷氨酸.采用MALDI-TOF质谱、红外光谱、紫外-可见光谱和1H NMR等方法对它们进行了结构表征.采用有机溶剂交换法,制备富勒烯氨基酸纳米颗粒水悬液,并进行了电镜和表面zeta-电位分析,结果表明,此水悬液体系稳定,颗粒形态大小均一,在生物医学领域中具有潜在的应用前景.Fullerene has been chemically functionalized by covalent attachment of different adducts onto the parent cage, to improve its solubility in polar organic solvents or to prepare aqueous solutions. This would be helpful for studying the biological activities of fullerene derivatives and their potential application in the biomedical field. N-Substituted 3,4-fullero pyrrolidine was synthesized via 1,3-dipolar cycloaddition of the azomethine ylide. Aspartic acid and glutamic acid with protected α-amino and α-carboxyl groups were reacted with the activated hydroxyl group of N-substituted 3,4-fullero pyrrolidine, respectively. The products were then deprotected, affording two novel fullerene α-amino acids, fullerene aspartic acid and fullerene glutamic acid. Their chemical structures were characterized via MALDI-TOF-MS, UV-Vis, FTIR and ^1H NMR. Furthermore, the aqueous nanoparticle suspensions of these fullerene amino acids were obtained by the method of organic solvent exchange, characterized by electron microscopy and zeta-potential analysis. The nanoparticle sizes of both fullerene amino acids were around 100 nm, with zeta-potentials of about 27 mV. The results indicate that these aqueous suspensions were rather stable with considerably homogeneous shape and size of nanoparticles, and thus were worthy of further investigating their potential application in the biomedical field.

关 键 词：富勒烯α-氨基酸 纳米颗粒水悬液 加成反应 缩合反应 

分 类 号：O621[理学—有机化学]