Lipase mediated new chemo-enzymatic synthesis of (RS)-, (R)-, and (S)-bunolol

Chirality. 2023 Nov 13. doi: 10.1002/chir.23627. Online ahead of print.ABSTRACTThe β-adrenergic receptor blocking agents are an important class of drug molecules. The present study reports a new chemo and chemo-enzymatic synthetic process for (RS)-, (R)-, and (S)-bunolol, one of the potent β-adrenergic receptor blocker. In chemo-enzymatic process, CAL L4777 lipase was employed for enantioselective kinetic resolution to synthesize the enantiopure (R)-alcohol and (S)-ester from the corresponding racemic alcohol. Thereafter, the corresponding (R)-alcohol and deacylated (S)-ester were treated with tert-butylamine to produce (S)- and (R)-bunolol, respectively. In chemical approach, epichlorohydrin (RS-, R-, and S-) was used as a starting material via respective (RS)-, (S)-, and (R)-glycidyl ether as intermediates for synthesis of enantiomeric (RS)-, (R)-, and (S)-bunolol. In comparison between two approaches, it was found that the chemo-enzymatic process was more effective and resulted in enantiomeric excess of 98% with 35% yield.PMID:37957841 | DOI:10.1002/chir.23627

Source: Chirality - November 14, 2023 Category: Molecular Biology Authors: Ravinder Reddy Patlolla Pulivarthi Deepthi Gajjala Raveena Khawlhring Rosangzuala Somarowthu Tejaswini Reddy Shetty Prakasham Linga Banoth Source Type: research