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Synthesis of 2-chloro-2′-deoxyadenosine by microbiological transglycosylation using a recombinant Escherichia coli strain

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Abstract

Cladribine (2-chloro-2′-deoxyadenosine) was synthesized using intact cells of the recombinant Escherichia coli strain producing Geobacillus stearothermophilus B-2194 thermostable purine-nucleoside phosphorylase II (EC 2.4.2.1). Use of the cells containing this thermostable enzyme allowed the process to be conducted at a temperature of 70°C, which provided the maximal concentrations of sparingly soluble substrates. The best results were obtained with 2-chloroadenine as a modified base. The highest yield of the target 2-chloro-2′-deoxyadenosine (up to 95% in the case of deoxyguanosine) was reached when using 2′-deoxypurines as donors of deoxyribose. Use of thymidine for these purposes required its considerable molar excess over 2-chloroadenine (up to 6:1), which is connected with a nonoptimal amount of endogenous thymidine phosphorylase, necessary for synthesis of deoxyribose-1-phosphate, in the transglycosylation reaction.

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Authors and Affiliations

  1. Pushchino Branch of the Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Pushchino, Moscow oblast, 142290, Russia

    S. A. Taran, K. N. Verevkina, S. A. Feofanov & A. I. Miroshnikov

  2. Institute of Biochemistry and Physiology of Microorganisms, Pushchino, Moscow oblast, 142290, Russia

    T. Z. Esikova

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  1. S. A. Taran
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  2. K. N. Verevkina
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  3. T. Z. Esikova
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  4. S. A. Feofanov
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  5. A. I. Miroshnikov
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Correspondence to S. A. Taran.

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Original Russian Text © S.A. Taran, K.N. Verevkina, T.Z. Esikova, S.A. Feofanov, A.I. Miroshnikov, 2008, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2008, Vol. 44, No. 2, pp. 181–186.

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Taran, S.A., Verevkina, K.N., Esikova, T.Z. et al. Synthesis of 2-chloro-2′-deoxyadenosine by microbiological transglycosylation using a recombinant Escherichia coli strain. Appl Biochem Microbiol 44, 162–166 (2008). https://doi.org/10.1134/S0003683808020063

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  • DOI: https://doi.org/10.1134/S0003683808020063

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