C. C. Cheng

5 The Chemistry and Biochemistry of C-Nucleosides

Publisher Summary This chapter discusses the C-nucleoside literature. With respect to the naturally occurring C-nucleosides, most work published since 1970 has been discussed. In reviewing work relevant to the synthesis of C-nucleosides, the various synthetic strategies that have been developed have been discussed. Numerous new compounds for biological testing have been achieved by modification of natural C-nucleosides. synthetic approaches to C-nucleosides have utilized preformed carbohydrates as starting material. Successful syntheses have involved: (a) direct linkage of preformed base and carbohydrate precursors; and/or (b) stepwise construction of a heterocyclic base onto a preformed carbohydrate derivative. The chapter discusses c-nucleosides in biology and medicine. The elegant biological experiments using formycin have made great contributions by calling attention to the subtle and critical roles conformation and conformational flexibility of biomolecules play in their normal functioning. Numerous, perhaps a majority, of the synthetic C-nucleosides are becoming available for study in biological systems.