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Abstract
Rhodotorula mucilaginosa was successfully applied as a biocatalyst for the enantioselective resolution of the racemic mixtures of heteroatom phosphonates derivatives, resulting in receiving the following enantiomers: (S)-1-amino-1(2-thienyl)methylphosphonic acid (Product 1) and (R)-1-amino-1-(3′pirydyl) methylphosphonic acid (Product 2). Biological synthesis of both products is reported for the first time. Pure (S)-1-amino-1-(2-thienyl)methylphosphonic acid (Product 1) was isolated with a conversion degree of 50% after 24 h of biotransformation was conducted on a laboratory scale under moderate conditions (1.55 mM of substrate 1, 100 mL of distilled water, 135 rpm, 25°C; Method A). The scale was enlarged to semi-preparative one, using a simplified flow-reactor (Method C; 3.10 mM of substrate 1) and immobilized biocatalyst. The product was isolated with a conversion degree of 50% just after 4 h of biotransformation. Amino-1-(3′pirydyl)methylphosphonic acid (Substrate 2) was converted according to novel procedure, by the immobilized biocatalyst - Rhodotorula mucilaginosa. The process was carried out under moderate conditions (3.19 mM – substrate 2 solution; Method C1) with the application of a simplified flow reactor system, packed with the yeasts biomass entrapped in 4% agar-agar solution. Pure (R)-amino-1-(3′pirydyl)methylphosphonic (50% of conversion degree) was received within only 48 h.
Highlights
Aminophosphonates are known as biologically active compounds (Lejczak and Kafarski, 2009)
PAL [Phenylalanine ammonia lyase (EC 4.3. 1.24)], responsible for the conversion of phenylalanine to trans-cinnamic acid and ammonia (D’Cunha et al, 1995; D’Cunha, 2005), is a base of the industrial production of L-phenylalanine by a microbiological method with Rhodotorula sp. (D’Cunha et al, 1995; D’Cunha, 2005). These fungal species are known as producers of D-amino acid oxidases (e.g., DAAO: EC 1.4.3.3) (Gabler et al, 2000; Fantinato et al, 2001; Pollegioni et al, 2008), crucial for the production of L-amino acids from the racemic mixtures of the substrates via enantioselective, oxidative deamination of the particular enantiomers of the substrates
For the first time thienyl derivative of amino phosphonic acid was received in an optically pure form as (S)-1-amino-1-(2-thienyl)methylphosphonic acid. To our knowledge it is the first biocatalytic which resulted in the obtaining of pure enantiomer of phosphonate derivative with sulfur atom incorporated in its side functionality
Summary
Aminophosphonates are known as biologically active compounds (Lejczak and Kafarski, 2009). These fungal species are known as producers of D-amino acid oxidases (e.g., DAAO: EC 1.4.3.3) (Gabler et al, 2000; Fantinato et al, 2001; Pollegioni et al, 2008), crucial for the production of L-amino acids from the racemic mixtures of the substrates via enantioselective, oxidative deamination of the particular enantiomers of the substrates. Rhodotorula mucilaginosa was applied to resolve the racemic mixtures of the phosphonates’ derivatives with the sulfur or nitrogen atoms incorporated into the side functionality These yeasts were chosen after the screening experiments showing its outstanding oxidative activity (data not shown). As a consequence of inventing a new immobilization method (in 4% of agar-agar solution) (R)-enantiomer was produced
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