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浙江大学学报（理学版）
浙江大学学报（理学版）  2020, Vol. 47 Issue (1): 95-100    DOI: 10.3785/j.issn.1008-9497.2020.01.014
化学     
高效液相色谱手性固定相法拆分BETTI碱及其衍生物对映体
支明玉1,2, 朱岩2
1.杭州职业技术学院，浙江杭州 310018
2.浙江大学 化学系，浙江杭州 310028
Enantioseparation of Betti bases on chiral stationary phase by HPLC
ZHI Mingyu1,2, ZHU Yan2
1.Hangzhou Vocational & Technical College, Hangzhou 310018, China
2.Department of Chemistry, Zhejiang University, Hangzhou 310028, China
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摘要： 在纤维素三（3,5-二甲基苯基氨基甲酸酯）（Chiralcel OD-H）和Pirkle型(R, R)-Whelk-O1手性柱上对手性氨基酚1-(α-氨基苄基)-2-萘酚（Betti 碱）及其衍生物1-(α-苄氨基苄基)-2-萘酚和1-(α-哌啶基苄基)-2-萘酚对映体分离进行了研究，分别考察了在正己烷流动相中，碱性添加剂、醇类添加剂的种类和浓度对手性拆分的影响。结果表明：溶质在Chiralcel OD-H柱上的分离效果好，而在(R, R)-Whelk-O1手性柱上只有1-(α-苄氨基苄基)-2-萘酚部分分离。研究了空间立体结构因素对手性分离的影响，初步探讨和比较了溶质在这2种手性柱上的手性识别机理。发现对(R, R)-Whelk-O1柱，溶质与固定相之间的吸引作用很小，而对于Chiralcel OD-H柱，溶质在手性空腔中的空间适应性很可能是手性识别的关键。
关键词： Betti 碱;  1-(α-苄氨基苄基)-2-萘酚;  1-(α-哌啶基苄基)- 2-萘酚;  手性固定相;  对映体分离    
Abstract: In this paper, the separation of 1-(α-aminobenzyl)-2-naphthol, 1-(α-benzylaminobenzyl)-2-naphthol and 1-(α-piperidylbenzyl)-2-naphthol is studied on two chiral columns-Chiralcel OD-H and (R,R)-Whelk-O1 chiral columns. The influence of the structures on the chiral separation is investigated. The influence of the mobile phase composition including the concentration and type of the alcohol modifiers and the basic additive in hexane, the separation factor (α) and the resolution (Rs) are studied. Then the two different chiral recognition mechanisms are discussed and compared. 1-(α-aminobenzyl)-2-naphthol and 1-(α-benzylaminobenzyl)-2-naphthol and 1-(α-piperidylbenzyl)-2-naphthol can be baseline separated on chiralcel OD-H using hexane-iso-propanol (95:5, v/v) as eluent under a flow rate of 0.5 mL·min－1 at 25 °C. On (R,R)-Whelk-O1, the attractive interactions between CSP and solute are the key factor for retention and chiral recognition, on chiralcel OD-H, the steric fit of solute into the chiral cavity maybe the predominant factor for the chiral recognition of 1-(α-benzylaminobenzyl)-2-naphthol and 1-(α-piperidylbenzyl)-2-naphthol.
Key words: Betti base    1-(α-benzylaminobenzyl)-2-naphthol    1-(α-piperidylbenzyl)-2-naphthol    chiral stationary phase    enantioseparation
收稿日期: 2019-05-07 出版日期: 2020-01-25
CLC:  O625.3  
基金资助: 浙江省自然科学基金资助项目(LY18C200001)；杭州市科技发展计划农业科研攻关专项（20130432B18）；2019杭州市第二轮优秀创新团队医药与新材料研发及技术转化创新团队项目支持.
通讯作者: ORCID:http://orcid.org/0000-0001-5481-3929，E-mail：zhuyan@zju.edu.cn.   
作者简介: 支明玉（1972—），ORCID:http://orcid.org/0000-0001-6989-6528，女，硕士，副教授，主要从事食品营养及其分析检测研究.
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引用本文:

支明玉, 朱岩. 高效液相色谱手性固定相法拆分BETTI碱及其衍生物对映体[J]. 浙江大学学报（理学版）, 2020, 47(1): 95-100.

ZHI Mingyu, ZHU Yan. Enantioseparation of Betti bases on chiral stationary phase by HPLC. Journal of Zhejiang University (Science Edition), 2020, 47(1): 95-100.

链接本文:

https://www.zjujournals.com/sci/CN/10.3785/j.issn.1008-9497.2020.01.014    或    https://www.zjujournals.com/sci/CN/Y2020/V47/I1/95

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