Śliżewska Agnieszka, Majewska Paulina, Żymańczyk-Duda Ewa
Department of Biochemistry, Molecular Biology and Biotechnology, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Stanisława Wyspiańskiego 27, 50-370 Wrocław, Poland.
Molecules. 2025 Jun 27;30(13):2767. doi: 10.3390/molecules30132767.
This study investigates the efficient and enantioselective hydrolysis of ester bonds through a series of biotransformations employing various photobiocatalysts. A racemic mixture of 1-phenylethyl acetate served as the model substrate. The described research identified three strains exhibiting the highest biocatalytic activity: (CCALA 129), (CCALA 76), and (CCALA 187). Their application led to the complete hydrolysis of the starting reagent, yielding both the unreacted ester and its corresponding alcohol in an enantioselective manner. Notably, the selectivity, expressed as S, reached an impressive value of 283 in certain outcomes. The photobiotransformations were conducted under varying conditions, with particular focus on two essential parameters: the duration of the process, crucial for kinetically controlled reactions, and light exposure, critical for light-dependent organisms. The representative results highlight the efficacy of these biocatalysts. For instance, using (CCALA 76), (CCALA 129), and (CCALA 187) facilitated the production of 1-()-phenylethanol with enantiomeric excesses (ee) of 89%, 88%, and 86%, respectively, at a conversion degree of approximately 50%. These processes also yielded an optically enriched mixture of the unreacted substrate, 1-()-phenylethyl acetate. Specifically, in the case of (CCALA 76), the ee of the unreacted ester reached up to 98%. Light exposure emerged as a key factor influencing selectivity factor (S). Adjusting this parameter allowed us to achieve an value of up to 283 for the formation of 1-()-phenylethanol with an ee > 99% when utilizing the (CCALA 129) strain. Furthermore, light intensity proved crucial for scaling up these processes. Significant results were obtained with , particularly at substrate concentrations ranging from 1 to 10 mM under limited exposure. Here, the conversion degree was 55%, the ee of the ()-alcohol was 86%, and the selectivity factor (S) value was 21.
本研究通过一系列使用各种光生物催化剂的生物转化反应，对酯键的高效对映选择性水解进行了研究。外消旋乙酸1-苯乙酯混合物用作模型底物。所描述的研究确定了三种表现出最高生物催化活性的菌株：（CCALA 129）、（CCALA 76）和（CCALA 187）。它们的应用导致起始试剂完全水解，以对映选择性方式生成未反应的酯及其相应的醇。值得注意的是，在某些结果中，以S表示的选择性达到了令人印象深刻的283值。光生物转化在不同条件下进行，特别关注两个关键参数：对于动力学控制反应至关重要的过程持续时间，以及对于依赖光的生物体至关重要的光照。代表性结果突出了这些生物催化剂的功效。例如，使用（CCALA 76）、（CCALA 129）和（CCALA 187）在转化率约为50%时，分别促进了对映体过量（ee）为89%、88%和86%的1-（）-苯乙醇的生产。这些过程还产生了未反应底物1-（）-苯乙酸乙酯的光学富集混合物。具体而言，在（CCALA 76）的情况下，未反应酯的ee高达98%。光照成为影响选择性因子（S）的关键因素。调整该参数使我们在使用（CCALA 129）菌株时，对于ee>99%的1-（）-苯乙醇的形成，S值高达283。此外，光强度被证明对于扩大这些过程的规模至关重要。使用时获得了显著结果，特别是在有限光照下底物浓度为1至10 mM的范围内。在此，转化率为55%，（）-醇的ee为86%，选择性因子（S）值为21。
