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

The 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. © 2023 Wiley Periodicals LLC.

Citation

Ravinder Reddy Patlolla, Pulivarthi Deepthi, Gajjala Raveena, Khawlhring Rosangzuala, Somarowthu Tejaswini, Reddy Shetty Prakasham, Linga Banoth. Lipase mediated new chemo-enzymatic synthesis of (RS)-, (R)-, and (S)-bunolol. Chirality. 2024 Jan;36(1):e23627

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PMID: 37957841

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