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Construction of Functional Molecules Using Cholic Acid as a Building Block

使用胆酸作为构建模块构建功能分子

基本信息

批准号：
12640553
负责人：
KOHMOTO Shigeo
金额：
$ 2.3万
依托单位：
CHIBA UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2000
资助国家：
日本
起止时间：
2000 至 2001
项目状态：
已结题

项目摘要

(1) Synthesis of bicyclocholaphanes and their recognition abilities.The aim of this research project is to prepare novel host compounds usings cholic acids, the cheap easily available steroid, as a building block for the selective recognition of biologically important molecules. The following three topics were investigated.By employing its characteristic features, the rigid L-shaped molecule with three hydroxyl groups on its inner surface, bicyclocholaphanes with several cavity sizes were prepared. They showed reasonable extractability toward ribonucleosides and sugars in liquid (chloroform) - liquid (water) extraction. Strong binding constants (10^4M^<-1>) were obtained for ribonucleoside in solid - liquid (chloroform) extraction by them. AZT, an important anti-viral agent especially for AIDS, was included inside the cavities of cholaphanes, which was characterized by ^1H-NMR titration.2) Comparison of recognition abilities of bicyclocholaphanes with the corresponding tripodants.Whether cyclic structures were really necessary as a potential host molecules, the tripodant-type host molecules possessing three cholic acid units attached to cyclotribenzylene (a rigid molecules) and trimesic acid were prepared and their recognition abilities toward nucleosides were examined. Roughly speaking, these tripodants showed poor recognition abilities except few cases. It seems to be these tripodants have too flexible conformations so that they cannot bind guest molecules well.(3) Synthesis of bicyclochopahanes with metal complex formation.The novel ligand possessing three cholic acid units and bipyridyl at the end was prepared for the formation of bicyclocholaphane by complex formation with ruthenium. The complex was characterized by its ESI-MS and absorption spectrum.

(1)双胆碱的合成及其识别能力。本研究项目的目的是利用胆酸这种廉价易得的类固醇来制备新的宿主化合物，作为选择性识别生物学上重要分子的基础。调查了以下三个主题。利用其固有的性质，制备了内表面有三个羟基的刚性l型分子，并具有不同的空腔大小。它们在液体（氯仿）-液体（水）萃取中对核糖核苷和糖具有合理的提取率。在固液（氯仿）萃取中，得到了核糖核苷的强结合常数（10^4M^<-1>）。AZT是一种重要的抗艾滋病药物，被发现存在于胆碱类化合物的空腔中，并通过核磁共振谱对其进行了表征。2)双胆碱类与相应三足类生物识别能力的比较。是否真的需要环状结构作为潜在的寄主分子，我们制备了具有三个胆酸单元的三足型寄主分子，并检测了它们对核苷的识别能力。粗略地说，除了少数情况外，这些三足动物的识别能力很差。似乎这些三足动物的构象太灵活了，所以它们不能很好地结合客体分子。(3)金属配合物合成双环硫烷。制备了具有三个胆酸单元和末端联吡啶的新型配体，用于与钌络合生成双胆碱。通过ESI-MS和吸收光谱对配合物进行了表征。