Serial β-Cyclodextrin Glycidyl Ether Derivatives: Synthesis, Characterization And Molecular Recognization

Cyclomaltoligoosaccharides(cyclodextrins CDs) are cyclic oligosaccharides comprised ofα-1, 4-linked glucose monomers,β-CD is composed of seven glucose monomers and is currently the most widely available CD of lowest cost , the character ofβ-CD's hydrophobic cavity and hydrophilic outer makes it act as a host and form inclusion complexes with varieties of guest molecules, including organic molecules, inorganic molecules, pharmaceutically active molecules and biological molecules. However,β-CD in their native state is rigid molecules and offers limited utility in term of size shape ofβ-CD, water solubility and availability of chemically usefully functional groups. In order to increase water solubility and chang its cavity's shape, chemical modification ofβ-CD is a available method to improve the physical and chemical characteristics ofβ-CD, a variety of cyclodextrins derivatives have been described and some derivatives have been introduced for pharmaceutical complexations and analysis applications.Five kinds of intermediates glycidyl ether, which were ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, amyl glycidyl ether and benzyloxy glycidyl ether, were obtained through a phase-transfer catalysis methodology using acyclic and benzyl alcohol and epichlorohydrin. By choosing 1.5 % and 30 % of sodium hydroxide solution as the environmental media, subsequent procedures were conducted with these intermediates andβ-cyclodextrin as raw materials. The obtained products were isolated with a self packed silica gel column chromatography, and their chemical structures were proved to be the mono 2 substituted (3-alkyloxy/benzyloxy-2-hydroxy)propyl-β-cyclodextrins (a1, b1, c1, d1 and e1) and mono 6 substituted (3-alkyloxy/benzyloxy-2-hydroxy)propyl-β-cyclodextrins (A1, B1, C1, D1and E1) by means of the TLC, IR, DSC, MS, 1HNMR and 13CNMR measurements.Using sulfanilic acid anhydrous and p-nitrobenzoic acid as the guests, the performances of inclusion complexes of (3-alkyloxy-2-hydroxyl)propyl-β-cyclodex trins were realized by using UV spectrum method and the complex models were established in this research. It was concluded that (3-alkyloxy-2-hydroxyl) propyl-β-cyclodextrins had better inclusion ability in low concentration of sodium hydroxide solution than in high concentration to sulfanilic acid anhydrous, furthermore, the inclusion ability of (3-alkyloxy-2-hydroxyl)propyl-β-cyclodextrins...