Abstract
The possibility of using Lecitase® Ultra as a novel alternative biocatalyst for the kinetic resolution of model racemic allyl esters of (E)-4-phenylbut-3-en-3-ol: Acetate (4a) and propionate (4b) through their enantioselective hydrolysis was investigated. Reaction afforded (+)-(R)-alcohol (3) and unreacted (−)-(S)-ester (4a or 4b). Hydrolysis of propionate 4b proceeded with higher enantioselectivity than acetate 4a. (R)-Alcohol (3) with highest enantiomeric excess (93–99%) was obtained at 20–30 °C by hydrolysis of propionate 4b, while the highest optical purity of unreacted substrate was observed for (S)-acetate 4a (ee = 34–56%). The highest enantioselectivity was found for the hydrolysis of propionate 4b catalyzed at 30 °C (E = 38). Reaction carried out at 40 °C significantly lowered enantiomeric excess of produced alcohol 3 and enantioselectivity in resolution. Lecitase® Ultra catalyzed the enantioselective hydrolysis of allyl esters 4a,b according to Kazlauskas’ rule to produce (R)-alcohol 3 and can find application as a novel biocatalyst in the processes of kinetic resolution of racemic allyl esters.
Highlights
Enantiomers of alcohols are widely used as building blocks in the synthesis of many biologically active compounds or directly as medicines [1], antifeedants [2], odorants [3], or pheromones [4]
® Ultra-mediated hydrolysis of we we present presentthethe preliminary results of Lecitase phenylbut-3-en-2-yl esters as the model substrates
Benzaldehyde 1 was subjected to propionate (4b) were obtained through a three-step synthesis
Summary
Enantiomers of alcohols are widely used as building blocks in the synthesis of many biologically active compounds or directly as medicines [1], antifeedants [2], odorants [3], or pheromones [4]. The wellestablished method for the production of enantiomerically enriched alcohols is their enzyme-catalyzed transesterification or hydrolysis of their racemic esters. For this purpose, commercially available lipases are commonly used to afford high enantioselectivity and enantiomeric purity of the products [5,6,7,8], but new biocatalysts are developed, among others phospholipases. Verapamil [19], Baclofen [20], or β-aryl substituted lactones with antiproliferative activity [21] Many their kinetic resolution transesterification [22,23,24,25] or hydrolysis [25,26].
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