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Asymmetric synthesis of (S)-ethyl-4-chloro-3-hydroxybutanoate using Candida parapsilosis ATCC 7330

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Journal of Industrial Microbiology & Biotechnology

Abstract

Asymmetric reduction of ethyl-4-chloro-3-oxobutanoate to (S)-ethyl-4-chloro-3-hydroxybutanoate in aqueous medium by resting cells of Candida parapsilosis ATCC 7330 was optimized. The influence of culture parameters (inoculum size, inoculum age and biocatalyst harvest time) and reaction parameters (co-substrate, resting cell, pH and substrate concentrations) on the asymmetric reduction were studied. It was found that these parameters significantly influenced the rate of the asymmetric reduction. Under the optimum conditions, the final concentration of (S)-ethyl-4-chloro-3-hydroxybutanoate, enantiomeric excess and the isolated yield of (S)-ethyl-4-chloro-3-hydroxybutanoate were 1.38 M (230 g/l), >99 and 95%, respectively. The space time yield was 115 mmol/lh, which is significantly higher than other whole cell biocatalysts reported so far.

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Acknowledgments

We thank the Department of Biotechnology, Government of India, for funding and the Sophisticated Analytical Instrumentation Facility (SAIF), IITM, for the NMR spectra.

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Authors and Affiliations

  1. Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology-Madras, Chennai, 600 036, India

    Tarjan Kaliaperumal & S. Kumar

  2. Applied and Industrial Microbiology Laboratory, Department of Biotechnology, Indian Institute of Technology-Madras, Chennai, 600 036, India

    Sathyanarayana N. Gummadi

  3. Laboratory of Bioorganic Chemistry, Department of Biotechnology, National Center for Catalysis Research, Indian Institute of Technology-Madras, Chennai, 600 036, India

    Anju Chadha

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  1. Tarjan Kaliaperumal
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  2. S. Kumar
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  3. Sathyanarayana N. Gummadi
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  4. Anju Chadha
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Corresponding authors

Correspondence to Sathyanarayana N. Gummadi or Anju Chadha.

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Kaliaperumal, T., Kumar, S., Gummadi, S.N. et al. Asymmetric synthesis of (S)-ethyl-4-chloro-3-hydroxybutanoate using Candida parapsilosis ATCC 7330. J Ind Microbiol Biotechnol 37, 159–165 (2010). https://doi.org/10.1007/s10295-009-0657-1

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  • DOI: https://doi.org/10.1007/s10295-009-0657-1

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