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Enantioselective resolution of 3-phenylthio-2-propanol with Humicola lanuginosa lipase

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Abstract

The acetylation of 3-phenylthio-2-propanol (168 mg) was performed with vinyl acetate (1 ml) using different lipases from 15 °C to 51 °C. As a result, the (R)-enantiomer was selectively acetylated and the (S)-enantiomer was non-reactive in all the cases. An appropriate choice of conditions can be made to isolate both (R)-alcohol (ee 99%, 36 h, conversion 46%, sub/enz: 1/2) and (S)-alcohol (ee 93%, 38 h, conversion 46%, THF, sub/enz: 1 l−1) using Humicola lanuginosalipase (Lipolase). Increasing the amount of enzyme increased the ee.

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Authors and Affiliations

  1. Department of Chemistry, Guru Nanak Dev University, Amritsar, 143 005, India

    Satwinder Singh, Subodh Kumar & Swapandeep Singh Chimni

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  1. Satwinder Singh
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  2. Subodh Kumar
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  3. Swapandeep Singh Chimni
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Singh, S., Kumar, S. & Chimni, S.S. Enantioselective resolution of 3-phenylthio-2-propanol with Humicola lanuginosa lipase. Biotechnology Letters 22, 1237–1241 (2000). https://doi.org/10.1023/A:1005609332450

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  • DOI: https://doi.org/10.1023/A:1005609332450

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