Optimisation, scope and advantages of the synthesis of chiral phenylethanols using whole seeds of Bauhinia variegata L. (Fabaceae) as a new and stereoselective bio-reducer of carbonyl compounds

• Published in: Biocatalysis and biotransformation Vol. 39; no. 2; pp. 109 - 123
• Main Authors: Demmel, Gabriela I., Bordón, Daniela L., Vázquez, Ana M., Decarlini, María F., Ruiz, Gustavo M., Cantero, Juan J., Rossi, Laura I., Aimar, Mario L.
• Format: Journal Article
• Language: English
• Published: Taylor & Francis 04.03.2021
• Subjects: Bauhinia variegata; Bioreduction; key intermediates; phenylethanols; seeds
• ISSN: 1024-2422; 1029-2446
• DOI: 10.1080/10242422.2020.1789115

With the aim of finding new methods for environmentally friendly synthesis of chiral phenylethanols, a screening was carried out to identify seeds that could be used as a biocatalyst capable of reducing stereoselectively prochiral ketones. As a result, seeds of Bauhinia variegata L. (Fabaceae) were identified as being an efficient and stereoselective biological reducer of acetophenone to produce (S)-1-phenylethanol (conversion of 98% and 99 e.e.%). Then, to optimise the reductive process, the effects of some variables such as temperature, load of substrate, pH, co-solvent, and reuse and storability of the seeds as a function of time were established. Utilising the optimal reaction conditions, nineteen substituted acetophenones were reduced to their corresponding chiral alcohols with a conversion ranging from 30% to 98% and enantiomeric excess of between 65% and >99%, and in addition, useful key intermediates were also obtained by the synthesis of drugs. The scope and advantages of this new biocatalytic synthetic method are also discussed. Research highlights A screening was carried out to identify seeds that could be used as a biocatalyst Seeds of Bauhinia variegata have been identified as an efficient biocatalyst to reduce carbonyl compounds. Acetophenone and substituted acetophenones were reduced with high stereoselectivity. Some key intermediates were synthetised using this methodology. Seeds can be stored for twenty-four months without loss of activity.