阴离子型β-环糊精衍生物的合成
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摘要
以β-环糊精与对甲苯磺酰氯反应制得6-对甲苯磺酰基-β-环糊精酯(1);1分别与牛磺酸和L-天冬氨酸反应合成了两个阴离子型β-环糊精衍生物单-6-牛磺酸-β-环糊精(2)和单-6-L-天冬氨酸-β-环糊精(3),总收率分别为56.1%和48.7%,其中化合物2未见文献报道,其结构经~1H NMR,~(13)C NMR和MS(ESI)表征。并对后处理过程进行了优化。
Mono-6-p-toluenesulfonyl-β-cyclodextrin ester(1) was prepared by reaction of β-cyclodextrin with p-toluenesulfonyl chloride. Two anionic β-cyclodextrin derivatives,mono-6-taurine β-cyclodextrin(2) and mono-6-L-aspartic acid β-cyclodextrin(3) with the total yield of 56. 1% and 48. 7%,were synthesized by reaction of 1 with taurine and L-aspartic ammonia acid,respectively. Compound 2 has not yet been reported in literature,and the structure was characterized by ~1H NMR,~(13)C NMR and MS(ESI). Furthermore,the post-processing was improved.
Mono-6-p-toluenesulfonyl-β-cyclodextrin ester(1) was prepared by reaction of β-cyclodextrin with p-toluenesulfonyl chloride. Two anionic β-cyclodextrin derivatives,mono-6-taurine β-cyclodextrin(2) and mono-6-L-aspartic acid β-cyclodextrin(3) with the total yield of 56. 1% and 48. 7%,were synthesized by reaction of 1 with taurine and L-aspartic ammonia acid,respectively. Compound 2 has not yet been reported in literature,and the structure was characterized by ~1H NMR,~(13)C NMR and MS(ESI). Furthermore,the post-processing was improved.
引文
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[17]李蛟,刘道杰.β-环糊精及其衍生物在分析化学中的应用进展[J].理化检验-化学分册,2003,39(6):372-376.
[18]孙乐,范晓东,刘郁杨,等.氨基酸修饰环糊精的合成及表征[J].应用化学,2008,25(4):405-408.
[19]ZHAO M X,ZHAO M,ZENG E Z,et al.Enhanced anti-cancer efficacy to cancer cells by doxorubicin loaded water-soluble amino acid-modifiedβ-cyclodextrin platinum complexes[J].Journal of Inorganic Biochemistry,2014,137:31-39.
[20]王用良,冯茹森,郭拥军,等.碱性水溶液中单6-氧-对甲苯磺酰-β-环糊精酯的非均相合成[J].应用化学,2011,28(11):1269-1273.
[2]廖才智.β-环糊精的应用研究进展[J].华工科技,2010,18(5):69-72.
[3]唐瑶,付柯,李翠,等.β-环糊精及其衍生物在食品添加剂中的应用[J].杭州化工,2015,(3):13-16.
[4]闫向伟.β-环糊精及其衍生物在生物制药领域中的应用[J].黑龙江科技信息,2016,(36):85-85.
[5]王小凤,顾艳丽,包保全,等.β-环糊精及其衍生物在靶向药物传递系统的研究进展[J].北方药学,2017,14(1):138-139.
[6]李琳琳,段尊斌,朱丽君,等.基于修饰的β-环糊精的超分子体系研究及应用进展[J].应用化学,2017,34(2):123-138.
[7]陆豪杰,阮宗琴,欧庆瑜.性添加剂磺丁基-β-环糊精的合成及毛细管电泳手性分离[J].分析测试学报,2000,19(5):16-19.
[8]袁瑞娟,王雄飞,詹雪艳,等.磺酸化-β-环糊精聚合物的合成及其在毛细管电泳手性拆分中的应用[J].分析化学,2013,41(4):559-564.
[9]靳慧,李方,顾峻岭,等.羧甲基-β-环糊精用于毛细管电泳中的手性分离[J].分析化学,1996(12):1387-1390.
[10]戴荣继,张姝,李方,等.水溶性β-环糊精衍生物的合成及其在毛细管电泳中的应用[J].化学学报,1998,56(6):594-599.
[11]李方,张莉萍,靳慧,等.以β-环糊精及其衍生物为手性选择剂毛细管电泳拆分几种药物的旋光对映体[J].分析化学,1997(6):644-647.
[12]LIU Y,YU H,ZHANG H,et al.Use of variousβ-cyclodextrin derivatives as chiral selectors for the enantiomeric separation of higenamine by capillary electrophoresis[J].Microchemical Journal,2017,134:289-294.
[13]VESCINA M C,FERMIER A M,GUO Y.Comparing cyclodextrin derivatives as chiral selectors for enantiomeric separation in capillary electrophoresis[J].Journal of Chromatography A,2002,973(1-2):187.
[14]ZHU B,XU S,GUO X,et al.Use of variousβ-cyclodextrin derivatives as chiral selectors for the enantiomeric separation of ofloxacin and its five related substances by capillary electrophoresis[J].Journal of Separation Science,2017,40(8):1784-1795.
[15]FILLET M,BECHET I,SCHOMBURG G,et al.Enantiomeric separation of acidic drugs by capillary electrophoresis using a combination of charged and unchargedβ-cyclodextrins as chiral selectors[J].Journal of Separation Science,2015,19(12):669-673.
[16]王兆昆,赵龙山,崔智,等.磺酸化-β-环糊精为手性选择剂分离5种β-受体阻断剂类药物[J].沈阳药科大学学报,2015(12):962-966.
[17]李蛟,刘道杰.β-环糊精及其衍生物在分析化学中的应用进展[J].理化检验-化学分册,2003,39(6):372-376.
[18]孙乐,范晓东,刘郁杨,等.氨基酸修饰环糊精的合成及表征[J].应用化学,2008,25(4):405-408.
[19]ZHAO M X,ZHAO M,ZENG E Z,et al.Enhanced anti-cancer efficacy to cancer cells by doxorubicin loaded water-soluble amino acid-modifiedβ-cyclodextrin platinum complexes[J].Journal of Inorganic Biochemistry,2014,137:31-39.
[20]王用良,冯茹森,郭拥军,等.碱性水溶液中单6-氧-对甲苯磺酰-β-环糊精酯的非均相合成[J].应用化学,2011,28(11):1269-1273.