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HPLC에서 다당 유도체를 기초로 한 키랄 컬럼을 이용한 거울상 이성질체의 광학분리

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Author(s)
윤원남
Issued Date
2013
Abstract
Part 1에서는 고성능 액체 크로마토그래피에서 키랄 선택자로 다당 유도체가 코팅된 키랄 컬럼과 공유결합 된 키랄 컬럼을 사용하여 여러 종류의 α-amino acid ester의 benzophenone imine의 광학분리를 수행하였다. Benzophenone imine 유도체 시료는 α-amino acid ester HCl, benzophenone imine Schiff base, magnesium sulfate anhydrous를 2-propanol 용매에 넣어 상온에서 반응시켜 준비하였다. 일반적으로 Chiralpak IC가 다른 컬럼들에 비해서 상당히 좋은 광학분리 결과를 보여주었다.
Part 2에서는 고성능 액체 크로마토그래피에서 다당 유도체가 공유결합 된 키랄 컬럼을 사용하여 다양한 α-amino acid ester를 NBD-Cl로 유도체화 한 화합물의 광학분리를 수행하였다. 이를 위한 NBD 유도체를 얻기 위해 α-amino acid ester HCl, NBD-Cl, sodium bicarbonate를 ethanol 용매에 반응시키는 매우 편리한 유도체화 방법을 개발하였다. NBD 유도체 물질들을 광학분리 한 결과, Chiralpak IA를 사용했던 경우 매우 훌륭한 광학분리 결과를 보여주었다. 또한 α-amino acid ester의 NBD 유도체의 분석은 UV detection보다 fluorescence detection에서 더 선택적이고 뛰어난 감도를 나타내는 것을 확인하였다.|In part 1, using several coated and covalently bonded chiral stationary phases (CSPs) from polysaccharide derivatives as chiral selector, the separation of α-amino acid esters as benzophenone imine derivatives is performed by HPLC. The benzophenone imine derivatives were prepared by stirring α-amino acid ester hydrochloride salts, benzophenone imine Schiff base, and magnesium sulfate anhydrous in 2-propanol. In general, the resolution of Chiralpak IC was superior to those of the other CSPs.
In part 2, the enantiomer separation of α-amino acid methyl esters as nitrobenzoxadiazole (NBD) derivatives was performed by normal HPLC using covalently immobilized chiral columns based on polysaccharide derivatives. The NBD derivatives were prepared by stirring α-amino acid methyl ester HCl and NBD-Cl with sodium bicarbonate in ethanol. The results of enantiomer separation of NBD derivatives, The performance of Chiralpak IA was superior to the other CSPs. In addition, analysis of NBD derivative of α-amino acid methyl ester was confirmed that the fluorescence detection is more selective and sensitive as compared with UV detection.
Alternative Title
The Enantiomer Separation Using Chiral Columns Based on Polysaccharides by HPLC
Alternative Author(s)
Yun, Wonnam
Affiliation
조선대학교 약학대학
Department
일반대학원 약학과
Advisor
이원재
Awarded Date
2014-02
Table Of Contents
국문초록 ………………………………………………………………………… ⅷ
Abstract ………………………………………………………………………… 41
THANKS TO …………………………………………………………………… 42


PART 1. Liquid Chromatographic Resolution of α-Amino Acid Esters as Benzophenone Imine Derivatives
Abstract ………………………………………………………………………… 1
1. Introduction ………………………………………………………………… 2
2. Materials and Methods …………………………………………………… 3
3. Results and Discussion ………………………………………………… 6
3.1. Enantiomeric separation of α-amino acid esters as benzophenone imine Schiff base derivatives ……………… 6
3.2. Effects of mobile phase on the separation of α-amino acid esters as benzophenone imine derivatives ………………… 16
4. Conclusion …………………………………………………………………… 18
5. Reference …………………………………………………………………… 19


PART 2. Liquid Chromatographic Enantiomer Separation of α-Amino Acid Esters as NBD derivatives
Abstract ………………………………………………………………………… 21
1. Introduction ………………………………………………………………… 22
2. Materials and Methods …………………………………………………… 24
3. Results and Discussion ………………………………………………… 27
3.1. The effects of solvents and bases on the separation of α-amino acid esters as NBD derivatives …………………… 27
3.2. The results of enantiomer separation of α-amino acid methyl esters as NBD derivatives …………………………… 31
4. Conclusion ………………………………………………………………… 38
5. Reference …………………………………………………………………… 39
Degree
Master
Publisher
조선대학교
Citation
윤원남. (2013). HPLC에서 다당 유도체를 기초로 한 키랄 컬럼을 이용한 거울상 이성질체의 광학분리.
Type
Dissertation
URI
https://oak.chosun.ac.kr/handle/2020.oak/11857
http://chosun.dcollection.net/common/orgView/200000264149
Appears in Collections:
General Graduate School > 3. Theses(Master)
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