高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (7): 1342.

• 研究论文 • 上一篇    下一篇

醇存在下R,S-1,1′-2-联萘酚对映体的环糊精手性识别研究

李伟1, 翟言强2, 郭磊3, 谢剑炜3   

  1. 1. 山西大学环境与资源学院, 太原 030006;
    2. 吕梁高等专科学校化学系, 吕梁 033000;
    3. 军事医学科学院毒物药物研究所, 北京 100850
  • 收稿日期:2008-11-19 出版日期:2009-07-10 发布日期:2009-07-10
  • 通讯作者: 谢剑炜, 男, 博士, 研究员, 博士生导师, 主要从事分子识别与手性分离分析、毒物分析、质谱分析等研究. E-mail: xiejw@bmi.ac.cn
  • 基金资助:

    国家自然科学基金(批准号: 20575078)资助.

Investigation of Chiral Recognition of β-Cyclodextrin Toward 1,1′-Bi-2-Naphthol Enantiomers in the Presence of Different Alcohols by Fluorescence and HPLC

LI Wei1, ZAI Yan-Qiang2, GUO Lei3, XIE Jian-Wei3   

  1. 1. College of Environmental Science and Resources, Shanxi University, Taiyuan 030006, China;
    2. Department of Chemistry, Lüliang Higher College, Lüliang 033000, China;
    3. Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China
  • Received:2008-11-19 Online:2009-07-10 Published:2009-07-10
  • Contact: XIE Jian-Wei. E-mail: xiejw@bmi.ac.cn
  • Supported by:

    国家自然科学基金(批准号: 20575078)资助.

摘要:

R,S-1,1′-2-联萘酚对映体为手性客体分子, 采用荧光探针法详细研究了各种醇对β-环糊精/(RS)-1,1′-2-联萘酚对映体的手性包络和手性荧光猝灭等性质的影响, 结果表明, 醇的存在可显著影响R,S-1,1′-2-联萘酚对映体与β-环糊精形成包络物的包络形式和包络常数. 通过与该对映体的β-环糊精手性固定相高效液相色谱拆分法比较研究结果表明, 醇等第三客体分子可显著影响环糊精对对映体化合物的手性选择性和分离度.

关键词: 手性识别; 环糊精; 联萘酚; 荧光; 高效液相色谱

Abstract:

The chiral recognition of β-cyclodextrin(β-CD) to R,S-1,1′-bi-2-naphthol(BiNOL) has been investigated by fluorescence probe spectroscopy and high performance liquid chromatography(HPLC) in the presence of various alcohols or mobile phases. The effects of alcohols on the chiral recognition of CD/R or S-BiNOL have been discussed based on the binding constants and quenching constants. Chiral discrimination in the quenching of R,S-BiNOL complexed to β-CD was observed with adding alcohols, belonging to static quenching. The inclusion interaction between R,S-BiNOL and β-CD was significantly affected with the addition of alcohols and phosphate salt, and leading to the chiral selection or chiral resolution enhanced. The results of two methods are consistent for the chiral recognition of β-CD/R,S-BiNOL inclusion. The chiral recognition mechanism of R,S-BiNOL by CD was well explained by these experiments.

Key words: Chiral recognition; Cyclodextrin; 1,1′-Bi-2-naphthol; Fluorescence; High performance liquid chromatography(HPLC)

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