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...

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Veröffentlicht in:Chirality (New York, N.Y.) N.Y.), 2024-01, Vol.36 (1), p.e23627-n/a
Hauptverfasser: Patlolla, Ravinder Reddy, Deepthi, Pulivarthi, Raveena, Gajjala, Rosangzuala, Khawlhring, Tejaswini, Somarowthu, Prakasham, Reddy Shetty, Banoth, Linga
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container_title Chirality (New York, N.Y.)
container_volume 36
creator Patlolla, Ravinder Reddy
Deepthi, Pulivarthi
Raveena, Gajjala
Rosangzuala, Khawlhring
Tejaswini, Somarowthu
Prakasham, Reddy Shetty
Banoth, Linga
description 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. In essence, the authors of the present work report an effective, straightforward chemical and chemo‐enzymatic synthetic technique for the production of enantiopure levobunolol. CAL L4777 enzyme, one of several lipases tested, efficiently catalyzed the reaction with a yield of 35% and an efficiency of 98% at 30°C and acyl donors of cyclohexane and vinyl acetate.
doi_str_mv 10.1002/chir.23627
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subjects Adrenergic beta-Antagonists
biocatalysis
Bunolol
chemo‐enzymatic synthesis
Esters
levobunolol
lipase
Lipase - chemistry
Receptors, Adrenergic, beta
Stereoisomerism
title Lipase mediated new chemo‐enzymatic synthesis of (RS)‐, (R)‐, and (S)‐bunolol
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