Chiral separation of terbutaline by supercritical fluid chromatography with peak purity determination by UPLC–MS and modeling for chiral recognition mechanism

Author:

Ali Imran1ORCID,Alam Syed Dilshad2,Raja Rupak3,Jain Arvind K3,Mustaqeem Mohd1,Locatelli Marcello4ORCID,Aboul‐Enein Hassan Y5,Yusuf Kareem6

Affiliation:

1. Department of Chemistry Jamia Millia Islamia New Delhi India

2. Jubilant Biosys Limited, Knowledge Park‐II Greater Noida India

3. Division of Chemistry, School of Basic and Applied Sciences Galgotias University Greater Noida India

4. Analytical and Bioanalytical Chemistry University "G. d'Annunzio" of Chieti‐Pescara, Department of Pharmacy, Build B, Level 2 Chieti Italy

5. Pharmaceutical and Medicinal Chemistry Department National Research Centre Cairo Egypt

6. Department of Chemistry, College of Science King Saud University Riyadh Saudi Arabia

Abstract

AbstractBACKGROUNDTerbutaline is the drug of choice for asthma patients but it exists in racemic mixture. (R)‐(−)‐terbutaline is 200 times more active than (S)‐(+)‐terbutaline yet it is not advisable to prescribe racemic mixture due to certain adverse effects of (S)‐(+)‐terbutaline. Therefore, a fast, effective and reproducible separation method is necessary.RESULTSChiral separation was achieved on Chiralpak‐IE and Chiralpak‐IG columns (250 × 4.6 mm, 5 μm) using carbon dioxide‐methanol (CO2‐MeOH, 60:40) with a 0.2% triethylamine mobile phase. The flow was 1.0 mL min−1 with detection at 223 nm using a photodiode array (PDA) detector. The values of retention, separation and resolution factors were in the ranges 1.88–2.38, 1.14–1.26 and 0.91–1.17, respectively; with best separation with Chiralpak‐IE. The tailing factors and number of theoretical plates were in the range of 1.0–1.23 and 487–3699. The purity of the separated peaks was determined by ultra‐performance liquid chromatography–mass spectrometry (UPLC–MS); indicating 100% purity of the peaks. The chiral recognition was determined by modeling with binding affinities −5.0 and −6.0 for S‐ and R‐enantiomers, respectively; indicating S‐enantiomer elution first followed by R‐enantiomers. The major forces responsible for the chiral resolution were hydrogen bonding and π‐π interactions.CONCLUSIONOwing to the great demand for optically active pure drugs and high economic pressure on analytical techniques, the chiral separation of terbutaline was achieved via inexpensive supercritical fluid chromatography. The reported method may be used to prepare optically active pure terbutaline drugs (R‐enantiomers) at a pilot scale. © 2024 Society of Chemical Industry (SCI).

Publisher

Wiley

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