Enantio- and chemoselective oxidation of omeprazole sulfide to enantiopure (S)-omeprazole with whole-cells of Aspergillus carbonarius
2018
Sangar, Shefali | Vaid, Bhavna | Jolly, Ravinder S.
Development of a biocatalytic method for the preparation of (S)-omeprazole (esomeprazole) in enantiomerically pure form is in great demand in pharmaceutical industry. A newly isolated fungal strain has been described, which converted omeprazole sulfide (5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio-1H-benzoimidazole) to (S)-enantiomer of omeprazole (5-Methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl-1H-benzimidazole) in > 95% e.e. The fungal strain was identified as Aspergillus carbonarius. A conversion of 91.8% was achieved at substrate concentration of 0.05 gmL−1 with the suspension of cells of A. carbonarius in phosphate buffer pH 8.0 at 30 °C. The bi°catalyst was chemoselective for oxidation of sulfide to sulfoxide as no trace of corresponding sulfone could be detected during the reaction.
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