Preparative scale application of Mucor circinelloides ene–reductase and alcohol dehydrogenase activity for the asymmetric bioreduction of α,β-unsaturated γ-ketophosphonates

• Published in: Bioorganic chemistry 2020-03, Vol.96, p.103548, Article 103548
• Main Authors: Janicki, Ignacy, Kiełbasiński, Piotr, Szeląg, Jakub, Głębski, Adrian, Szczęsna-Antczak, Mirosława
• Format: Article
• Language: English
• Subjects: Alcohol Dehydrogenase - metabolism; Asymmetric catalysis; Biocatalysis; Biotransformation; Catalysis; Chiral phosphonates; Culture Media; Enzymes; Mucor - enzymology; Organophosphonates - metabolism; Oxidation-Reduction; Oxidoreductases - metabolism; Stereoisomerism; Substrate Specificity
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2019.103548

[Display omitted] •Mucor circinelloides was applied for asymmetric biotransformation of phosphonates (1).•Products of CC double bond and/or CO group reduction (2 and 3) were obtained in good yields.•All products were obtained with excellent enantiomeric excess – up to >99% ee.•Biotransformation outcome (2:3 product ratio) is dependent on the growth media applied.•Cheap growth medium (corn steep liquor) can be successfully applied for the biotransformation. The fungus Mucor circinelloides exhibits high potential for green chemistry and technological applications. Recently M. circinelloides, which so far was considered mainly as a platform for biodiesel production, was found to exhibit high ene-reductase activity. In our current research we applied this promising microorganism to the biotransformation of a series of α,β-unsaturated γ-ketophosphonates. The biotransformations were conducted using cheap corn steep liquor or minimal media. The products were obtained with excellent enantiomeric purity (>99% ee in most cases) and in good isolated yields, highlighting the great potential of this microorganism for asymmetric synthesis. Moreover, the products obtained may be further applied as chiral building blocks for the synthesis of biologically active compounds, such as glutamic acid or fosmidomycin derivatives.