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Novel biocatalyst for productions of S-(-)-2-[6-benzyloxy -2,5,7,8-tetramethylchroman -2-yl] ethanol—precursor of natural α-tocols

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Abstract

A novel promising strain of actinobacteria Rhodococcus sp. 77-32 was identified. Its acetonetreated biomass the could be used as a biocatalyst for production of S-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (S-BCE), a precursor of natural α-tocols. It was established that a reaction of enantioselective hydrolysis of racemic (±)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman (BCEA) occurred in the phosphate buffer–acetone system, resulting in enrichment of the residual substrate by S-enantiomer (S-(+)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman, S-BCEA). It was shown that the hydrolysis was accompanied by stereoinversion of the formed product, R-(+)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl] ethanol (R-BCE), into the S-BCE. The transformation conditions (acetone content, acidity, temperature, reaction duration) were optimized, providing simultaneous production of optically pure S-BCE and S-BCEA with an almost quantitative yield.

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Authors and Affiliations

  1. Ufa State Petroleum Technologcal University, Ufa, 450062, Russia

    N. I. Petukhova, I. I. Kon’shina & V. V. Zorin

  2. Institure of Petrleum Chemistry and Catalysis, Russian Academy of Sciences, Ufa, 450075, Russia

    A. Yu. Spivak & V. N. Odinokov

Authors
  1. N. I. Petukhova
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  2. I. I. Kon’shina
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  3. A. Yu. Spivak
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  4. V. N. Odinokov
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  5. V. V. Zorin
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Correspondence to N. I. Petukhova.

Additional information

Original Russian Text © N.I. Petukhova, I.I. Kon’shina, A.Yu. Spivak, V.N. Odinokov, V.V. Zorin, 2017, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2017, Vol. 53, No. 2, pp. 188–195.

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Petukhova, N.I., Kon’shina, I.I., Spivak, A.Y. et al. Novel biocatalyst for productions of S-(-)-2-[6-benzyloxy -2,5,7,8-tetramethylchroman -2-yl] ethanol—precursor of natural α-tocols. Appl Biochem Microbiol 53, 187–193 (2017). https://doi.org/10.1134/S0003683817020144

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  • DOI: https://doi.org/10.1134/S0003683817020144

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