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Chemical Transformations of the Sugar Moiety of Nucleosides

  • Chapter
Nucleoside Analogues

Part of the book series: NATO Advanced Study Institutes Series ((NSSA,volume 26))

Abstract

The last two decades have witnessed the proliferation of a rather vast literature concerning the synthesis and biological properties of nucleoside analogues. These interesting compounds can be roughly subdivided into two major groups--those containing modified heterocyclic bases, and those in which the sugar moiety has been altered and is no longer ribose or 2-deoxyribose as found in nucleic acids. Base analogues have in general been prepared either via N-glycosidation of suitably modified heterocycles or by structural transformations of the base moiety in existing nucleosides. Both of these approaches will be considered in detail during this meeting by my colleagues Drs. Vorbrüggen, Robins and Townsend. In a related way, nucleosides containing modified carbohydrate moieties have frequently been prepared via glycosidation of an appropriate purine or pyrimidine base with a suitable derivative of the desired sugar. Alternatively, a great deal of effort has been devoted to the development of specific chemical transformations suitable for introducing the desired modifications into the sugar moiety of intact nucleosides. It is this latter approach that has particularly fascinated the group in our laboratory and that I wish to review for you today.

Contribution No. 527 from the Institute of Organic Chemistry, Syntex Research, Palo Alto, California, U.S.A.

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  1. Institute of Organic Chemistry, Syntex Research, 3401 Hillview Avenue, Palo Alto, California, USA

    J. G. Moffatt

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  1. The University of Birmingham, Birmingham, UK

    Richard T. Walker

  2. Katholieke Universiteit Leuven, Leuven, Belgium

    Erik De Clercq

  3. Max-Planck Institut für Experimentelle Medizin, Göttingen, West Germany

    Fritz Eckstein

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Moffatt, J.G. (1979). Chemical Transformations of the Sugar Moiety of Nucleosides. In: Walker, R.T., De Clercq, E., Eckstein, F. (eds) Nucleoside Analogues. NATO Advanced Study Institutes Series, vol 26. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9137-5_4

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