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New insights on nucleoside 2′-deoxyribosyltransferases: a versatile Biocatalyst for one-pot one-step synthesis of nucleoside analogs

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Abstract

In recent years, glycosiltransferases have arisen as standard biocatalysts for the enzymatic synthesis of a wide variety of natural and non-natural nucleosides. Such enzymatic synthesis of nucleoside analogs catalyzed by nucleoside phosphorylases and 2′-deoxyribosyltransferases (NDTs) has demonstrated to be an efficient alternative to the traditional multistep chemical methods, since chemical glycosylation reactions include several protection–deprotection steps. This minireview exhaustively covers literature reports on this topic with the final aim of presenting NDTs as an efficient option to nucleoside phosphorylases for the synthesis of natural and non-natural nucleosides. Detailed comments about structure and catalytic mechanism of described NDTs, as well as their possible biological role, substrate specificity, and advances in detection of new enzyme specificities towards different non-natural nucleoside synthesis are included. In addition, optimization of enzymatic transglycosylation reactions and their application in the synthesis of natural and non-natural nucleosides have been described. Finally, immobilization of NDTs is shown as a practical procedure which leads to the preparation of very interesting biocatalysts applicable to industrial nucleoside synthesis.

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Acknowledgments

I thank all my colleagues in the Biochemistry and Molecular Biology I Department (Complutense University of Madrid, Spain) and in the Biotechnology and Pharmacy Department (European University of Madrid, Spain), and finally I specially thank Dr. Pierre Alexandre Kaminski (Pasteur Institute) for all the good advices and for his availability to discuss experimental results.

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Authors and Affiliations

  1. Departamento de Bioquímica y Biología Molecular I, Facultad de Ciencias Biológicas, Universidad Complutense de Madrid, c/ José Antonio Novais 2, 28040, Madrid, Spain

    A. Fresco-Taboada, I. de la Mata, M. Arroyo & J. Fernández-Lucas

  2. Departamento de Farmacia y Biotecnología, Facultad de Ciencias Biomédicas, Universidad Europea de Madrid, Urbanización El Bosque, c/ Tajo s/n, 28670, Villaviciosa de Odón, Madrid, Spain

    J. Fernández-Lucas

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  1. A. Fresco-Taboada
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  2. I. de la Mata
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  4. J. Fernández-Lucas
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Correspondence to J. Fernández-Lucas.

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Fresco-Taboada, A., de la Mata, I., Arroyo, M. et al. New insights on nucleoside 2′-deoxyribosyltransferases: a versatile Biocatalyst for one-pot one-step synthesis of nucleoside analogs. Appl Microbiol Biotechnol 97, 3773–3785 (2013). https://doi.org/10.1007/s00253-013-4816-y

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