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Regioselective enzymatic procedure for preparing 3′-O-stearoyl-6-azauridine by using Burkholderia cepacia lipase

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Abstract

Previous studies on the lipase-mediated acylation of 6-azauridine with vinyl stearate in organic solvents revealed that while preparing a potential prodrug, 3′-O-stearoyl-6-azauridine, a lipase from Burkholderia cepacia showed high regioselectivity toward the second hydroxyl group. The most suitable reaction solvent, molar ratio of vinyl stearate to 6-azauridine, and reaction temperature were anhydrous acetone, 15:1, and 45°C, respectively. Under these conditions, the initial reaction rate, 3′-regioselectivity, and maximum substrate conversion were as high as 10.4 mM/h, 86.0, and 99.0%, respectively.

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Authors and Affiliations

  1. School of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huai’an, 223-003, China

    Zhao-Yu Wang & Yan-Hong Bi

  2. Lab of Applied Biocatalysis, South China University of Technology, Guangzhou, 510-640, China

    Min-Hua Zong

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  1. Zhao-Yu Wang
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  2. Yan-Hong Bi
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Correspondence to Min-Hua Zong.

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Wang, ZY., Bi, YH. & Zong, MH. Regioselective enzymatic procedure for preparing 3′-O-stearoyl-6-azauridine by using Burkholderia cepacia lipase. Biotechnol Bioproc E 17, 393–397 (2012). https://doi.org/10.1007/s12257-011-0483-y

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  • DOI: https://doi.org/10.1007/s12257-011-0483-y

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