Fungal platform for direct chiral phosphonic building blocks production. Closer look on conversion pathway.

Ewa Żymańczyk-Duda,Magdalena Klimek-Ochab,Małgorzata Brzezińska-Rodak,Kinga Kozyra

doi:10.1007/s12010-014-1356-6

Ewa Żymańczyk-Duda, Magdalena Klimek-Ochab + Show 2 more

Open Access

https://doi.org/10.1007/s12010-014-1356-6

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Abstract

The application of Rhodospirillum toruloides strain allowed resolving the chemically synthesized racemic mixtures of following chiral aminophosphonic acids: 1-aminoethylphosphonic acid (1), 1-amino-1-iso-propyl-1-phosphonic acid (2), 1-amino-1-phenylmethylphosphonic acid (4) and 1-amino-2-phenylethylphosphonic acid (3). The applied protocols resulted in obtaining pure (R)-1-aminoethylphosphonic acid (100 % of e.e.) and enantiomerically enriched mixtures of other phosphonates (73 % e.e. of (S)-1-amino-1-phenylmethylphosphonic acid, 51 % e.e. of (R)-1-amino-2-phenylethylphosphonic acid and 40 % e.e. of (S)-1-amino-2-methylpropylphosphonic acid). Products are valuable chiral building blocks and serve as aminophosphonic acids platform for further applications. Performed experiments allowed to define the path of xenobiotics bioconversion.

Highlights

Aminophosphonic acids are organophosphorus compounds of variable biological activities as indicated before [1, 2]
Phosphonic and carboxylic acid differ considerably with respect to shape, size and acidity, α-aminophosphonic acids are considered as structural analogues of amino acids or as mimetics of the transition state of enzymatic peptide bond hydrolysis
Aminophosphonic acids are applied in hydrometallurgy for metal extraction and in diagnostic medicine as screening agents [6]

Summary

Introduction

Aminophosphonic acids are organophosphorus compounds of variable biological activities as indicated before [1, 2]. Phosphonic and carboxylic acid differ considerably with respect to shape, size and acidity, α-aminophosphonic acids are considered as structural analogues of amino acids or as mimetics of the transition state of enzymatic peptide bond hydrolysis. As a consequence, they exhibit inhibitory activity against different enzymes, especially towards proteinases such as the HIV protease, thrombin, aminopeptidases and human collagenase [3,4,5]. Aminophosphonic acids are applied in hydrometallurgy for metal extraction and in diagnostic medicine as screening agents [6] As it is known, particular biological activity of specific chiral compound is usually related to its absolute configuration [7]. On account of different biological and chemical applications of phosphonates (Fig. 1), development of effective synthetic methodologies for their preparation in optically pure forms has been a matter of interest for several research groups and is still not a fully explored field of science [8,9,10,11,12,13,14,15]

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