title: Preparation of cyclodextrin chiral stationary phases by organic soluble catalytic 'click' chemistry.
abstract: We describe an effective and simple protocol that uses click chemistry to attach native β-cyclodextrin (β-CD) to silica particles, resulting in a chiral stationary phase (CCNCSP) that can be used for the enantioseparation of chiral drugs by high-performance liquid chromatography (HPLC). Starting from β-CD, the CCNCSP is prepared in several steps: (i) reaction of β-CD with 1-(p-toluenesulfonyl)-imidazole to afford mono-6-toluenesulfonyl-β-CD; (ii) azidolysis of mono-6-toluenesulfonyl-β-CD in dimethylformamide to give mono-6-azido-β-CD (N(3)-CD); (iii) reaction of cuprous iodide with triphenylphosphine to form an organic soluble catalyst CuI(PPh(3)); (iv) preparation of alkynyl-modified silica particles; and (v) click chemistry immobilization of N(3)-CD onto alkynyl-modified silica to afford the desired chiral stationary phase. Synthesis of the stationary phase and column packing takes ∼1 week.
authors: School of Chemical and Biomedical Engineering, Nanyang Technological University, Singapore, Singapore.
authors: Yong
authors: Y
authors: Wang
authors: Hui
authors: H
authors: Chen
authors: Yin
authors: Y
authors: Xiao
authors: Cheong Hengq
authors: CH
authors: Ng
authors: Ting Shan
authors: TS
authors: Oh
authors: Timothy Thatt Yang
authors: TT
authors: Tan
authors: Siu Choon
authors: SC
authors: Ng
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D057930:Click Chemistry / Q000295:instrumentation / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003505:Cyclodextrins; D004364:Pharmaceutical Preparations; D012822:Silicon Dioxide