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Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

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Synthesis of Quinoline-Based New Chiral Derivatizing Reagents and its use in the Derivatization and Enantioseparation of Few Structurally Similar β-Blockers using Liquid Chromatography and Structural Optimization using DFT

https://doi.org/10.14233/ajchem.2023.28037
Raffiunnisa
Department of Chemistry, Aditya Engineering College, Surampalem-533437, India
N. Jaishetty
Department of Chemistry, SRM Institute of Science & Technology, Kattankulathur-603203, India
P. Ganesh
Department of Inorganic and Analytical Chemistry, Andhra University, Visakhapatnam-530003, India
M.S. Patel
Foundation Year Department, Mohammed Al-Mana College for Medical Sciences, Dammam, Kingdom of Saudi Arabia
V.S. Talismanov
Depatment of Chemistry, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, 141701, Russian Federation
S. Alwera
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, India
https://orcid.org/0000-0002-5897-2166
S. Sehlangia
Department of Chemistry, National Changhua University of Education, Changhua, Taiwan
https://orcid.org/0000-0001-7857-9583

Corresponding Author(s) : S. Sehlangia

sumanyadav1708@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

Abstract

In this work, quinoline based new chiral derivatizing reagent was synthesized by introducing chiral amino acid (L-proline) in the molecule. Synthesized chiral derivatizing reagent was characterized by spectroscopic techniques (1H NMR, FT-IR, HRMS and CHNS analysis) and used in the synthesis of diastereomer of chosen β-blockers. The RP-HPLC system was used to separate synthesized diastereomers (indirect approach of enantioseparation). Acetonitrile and buffer solution was used as mobile phase for analysis. The effect of varying concentrations and pH of mobile phase was optimized for the separation of diastereomers. The density functional theory calculations were also carried out to develop the lowest energy-minimize optimized diastereomer structures and to design separation mechanisms and elution orders. The retention factor (k), selectivity factor (α), resolution factor (RS), the limit of detection (0.192 ng mL–1) and the limit of quantification (0.576 ng mL–1) were calculated in the context of the method’s validation in accordance with ICH guidelines.

Keywords

Quinoline β-Blockers Indirect-enantioseparation Chiral derivatizing reagents RP-HPLC
Raffiunnisa, Jaishetty, N., Ganesh, P., Patel, M., Talismanov, V., Alwera, S., & Sehlangia, S. (2023). Synthesis of Quinoline-Based New Chiral Derivatizing Reagents and its use in the Derivatization and Enantioseparation of Few Structurally Similar β-Blockers using Liquid Chromatography and Structural Optimization using DFT. Asian Journal of Chemistry, 35(8), 1855–1861. https://doi.org/10.14233/ajchem.2023.28037
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