- P-ISSN 1225-0163
- E-ISSN 2288-8985
- P-ISSN1225-0163
- E-ISSN2288-8985
- SCOPUS, ESCI, KCI
Article Detail
Home > Article Detail
1H-NMR and HPLC analysis on the chiral discrimination of β-blockers using (S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid
Analytical Science and Technology / Analytical Science and Technology, (P)1225-0163; (E)2288-8985
2021, v.34 no.1, pp.9-16
https://doi.org/10.5806/AST.2021.34.1.9
(College of Pharmacy, Kangwon National University)
(Faculty of Pharmacy, Ho Chi Minh City University of Technology)
(College of Pharmacy, Kangwon National University)
(College of Pharmacy, Kangwon National University)
(Faculty of Pharmacy, Ho Chi Minh City University of Technology)
(College of Pharmacy, Kangwon National University)
(College of Pharmacy, Kangwon National University)
Sang,
H.
S.
, Xuan-Lan,
M.
, Thi-Anh-Tuyet,
L.
, &
Kyeong,
H.
K.
(2021). 1H-NMR and HPLC analysis on the chiral discrimination of β-blockers using (S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid. Analytical Science and Technology, 34(1), 9-16, https://doi.org/10.5806/AST.2021.34.1.9
- Downloaded
- Viewed
Abstract
In the group of commonly prescribed β-blocker drugs, one of the enantiomers is generally relatively more active than the others. This study aims to develop a technique for the chiral analysis of select β-blockers based on proton nuclear magnetic resonance (1H-NMR) spectrometry. (S)-2-Tert-butyl-2-methyl-1,3-benzodioxole-4- carboxylic acid ((S)-TBMB) was synthesized and utilized as a chiral derivatizing agent. Pure β-blocker enantiomers were isolated from racemates by semi-preparative liquid chromatography prior to derivatization. The reaction time and concentration of (S)-TBMB were controlled to improve the derivatization procedure. No racemization was found during the analysis. High-performance liquid chromatography (HPLC) analysis was also performed for comparative purposes. High agreement between the NMR and HPLC methods was achieved in the determination of (R)-metoprolol in a standard solution of the (S) isomer.
- keywords
- <TEX>${\beta}$</TEX>-blockers, Chiral derivatizing agent, <TEX>$^1H$</TEX>-NMR, HPLC
Reference
1
1. W. H. Frishman, A. Cheng-Lai and J. Nawarskas, ‘Current Cardiovascular Drugs’, 4th Ed., Current Medicine, Philadelphia, 2005.
2
2. W. S. Knowles, R. Noyori and K. B. Sharpless, ‘The Nobel Prize in Chemistry 2001’, https://www.nobelprize. org/prizes/chemistry/2001/summary/, Assessed 7Apr 2020.
3
3. L. A. Nguyen, H. He and C. Pham-Huy, Int. J. Biomed. Sci., 2(2), 85-100 (2006).
4
4. U.S. Food and Drug Administration, ‘Development of New Stereoisomeric Drugs’, https://www.fda.gov/regulatoryinformation/search-fda-guidance-documents/developmentnew-stereoisomeric-drugs, Assessed 7 Apr 2020.
5
5. M. Ogrodowczyk, K. Dettlaff and A. Jelinska, MiniReviews Med. Chem., 16(1), 40-54 (2016).
6
6. V. K. Vashistha and A. Kumar, Chirality, 32(5), 722-735 (2020).
7
7. R. Gonçalves, C. Ribeiro, S. Cravo, S. C. Cunha, J. A. Pereira, J. O. Fernandes, C. Afonso and M. E. Tiritan, J. Chromatogr. B, 1125, 121731-121741 (2019).
8
8. P. Malik and R. Bhushan, J. Chromatogr. B, 1061, 117-122 (2017).
9
9. G. Egginger, W. Lindner, C. Vandenbosch and D. L. Massart, Biomed. Chromatogr., 7(6), 277-295 (1993).
10
10. S. Batra and R. Bhushan, Biomed. Chromatogr., 33, 4370-4385 (2019).
11
11. S. Batra and R. Bhushan, Biomed. Chromatogr., 32, 4090-4110 (2018).
12
12. E. I. El-Kimary and M. A. A. Ragab, Chirality, 30(11), 1195-1205 (2018).
13
13. A. E. Bodoki, B. C. Iacob, L. E. Gliga, S. L. Oprean, D. A. Spivak, N. A. Gariano and E. Bodoki, Molecules, 23(8), 1875-1894 (2018).
14
14. Y. Zhao, S. Li, X. Wang, J. Yu, Y. Song and X. Guo, Chirality, 31(7), 502-512 (2019).
15
15. M. Li, Z. Jiang, X. Di and Y. Song, Biomed. Chromatogr., 34(5), 4803-4810 (2020).
16
16. K. F. Morris, E. J. Billiot, F. H. Billiot, C. B. Hoffman, A. A. Gladis, K. B. Lipkowitz, W. M. Southerland and Y. Fang, Chem. Phys., 457, 133-146 (2015).
17
17. M. Silva, S. Morante-Zarcero, D. Pérez-Quintanilla, M. L. Marina and I. Sierra, Electrophoresis, 38(15), 1905-1912 (2017).
18
18. Y. Liu, L. L. Sombra and P. W. Stege, Chirality, 30(8), 988-995 (2018).
19
19. J. Guo, J. Wang, H. Lin, Y. Feng, H. Shen, R. Huang, L. Liu and Z. Zhao, J. Sep. Sci., 42(5), 1077-1087 (2019).
20
20. F. Akter and S. A. Shamsi, J. Chromatogr. A, 1617, 460835-460846 (2020).
21
21. J. Il Sung, N. Van Thi Nguyen, M. J. Park, S. B. Lee, Y. J. Lee, S. H. Choi and K. H. Kim, Arch. Pharm. Res., 33(9), 1301-1306 (2010).
22
22. G. M. Hanna and C. A. Lau-Cam, J. Pharm. Biomed. Anal., 13(11), 1313-1319 (1995).
23
23. S. Lee and S. Jung, Carbohydr. Res., 337(19), 1785-1789 (2002).
24
24. T. Ishizu, H. Tsutsumi, E. Yokoyama, H. Tanabe and A. Yokoyama, Chem. Pharm. Bull., 64(2), 142149 (2016).
25
25. R. B. Yu and J. P. Quirino, Molecules, 24(6), 1135-1152(2019).
26
26. H. Meguro, J. H. Kim, C. Bai, Y. Nishida and H. Ohrui, Chirality, 13(8), 441-445 (2001).
27
27. Y. Nishida, H. Ohrui and H. Meguro, Tetrahedron Lett., 30(39), 5277-5280 (1989)
Other articles from this issue
- Development and validation of an analytical method for the quantification of 2,6-diisopropylnaphthalene in agricultural products using GC-MS/MS
- 1H-NMR and HPLC analysis on the chiral discrimination of β-blockers using (S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid
- FT-IR analysis of flame resistant chemical mixture
- Removal of residual VOCs in a collection chamber using decompression for analysis of large volatile sample
- more
Recommanded Articles
This website recommended the use the Chrome browser for journal website.