1 The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides

https://doi.org/10.1016/S0079-6468(08)70228-5Get rights and content

Publisher Summary

This chapter reviews recent advances in the chemistry and biochemistry of C-nucleosides, the literature concerning C-arylglycoside (i.e., nonnitrogen heterocyclic C-nucleoside) antibiotics, and recent significant advances in the synthesis of C-nucleosides and C-glycosides. It also discusses biological test data and data that are relevant to structure–activity relationships. Modification of readily available natural C-nucleosides is an attractive route to new C-nucleoside analogs and derivatives, because one starting material often possesses much of the desired functionality and chiral properties. The chapter illustrates this approach with examples. The most frequently used strategy for C-nucleoside synthesis involves the construction of a heterocyclic aglycone from the C-1 substituent of a functionalized sugar intermediate.

References (376)

  • G.D. Daves et al.

    Prog. Med. Chem.

    (1976)
  • S. Hanessian et al.

    Adv. Carbohydr. Chem. Biochem.

    (1976)
  • R.J. Suhadolnik

    Prog. Nucleic Acid Res. Mol. Biol.

    (1979)
  • J.L. Sussman et al.

    J. Mol. Biol.

    (1978)
  • S.R. Holbrook et al.

    J. Mol. Biol.

    (1978)
  • H. Pang et al.

    J. Biol. Chem.

    (1982)
  • A. Matsuda et al.

    Carbohydr. Res.

    (1982)
  • T. Sato et al.

    Tetrahedron Lett.

    (1978)
  • T. Sato et al.

    Tetrahedron Lett.

    (1979)
  • T. Sato et al.

    Tetrahedron Lett.

    (1980)
  • T. Sato et al.

    Tetrahedron Lett.

    (1980)
  • M.S. Zedeck

    Biochem. Pharmacol.

    (1979)
  • K.A. Watanabe et al.

    Chem.-Biol. Interact.

    (1981)
  • P.A. Jones et al.

    Cell

    (1980)
  • K. Sakata et al.

    Tetrahedron Lett.

    (1975)
  • K. Isono et al.

    FEBS Lett.

    (1977)
  • S. Hara et al.

    Biochim. Biophys. Acta

    (1981)
  • T. Muller et al.

    FEBS Lett.

    (1981)
  • J.C. Niedzwicki et al.

    Biochem. Pharmacol.

    (1983)
  • Y. Uehara et al.

    Biochem. Pharmcol.

    (1981)
  • J. Arendes et al.

    Cancer Lett.

    (1978)
  • T. Sato et al.

    Tetrahedron Lett.

    (1978)
  • A.M. Mubarak et al.

    Tetrahedron Lett.

    (1981)
  • K. Sakata et al.

    Agr. Biol. Chem.

    (1977)
  • R.J. Suhadolnik

    Nucleosides as Biological Probes

    (1979)
  • J.J. Fox et al.

    Colloq.-Inst. Natl. Saute Rech. Med.

    (1978)
  • J.G. Buchanan

    Fortschr. Chem. Org. Natur.

    (1983)
  • J.G. Buchanan et al.

    Topics Antibiot. Chem.

    (1982)
  • J. Goodchild

    Topics Antibiot. Chem.

    (1982)
  • S.R. James

    J. Carbohydr. Nucleosides, Nucleotides

    (1979)
  • J.M.J. Tronchet

    Colloq.-Inst. Natl. Saute Rech. Med.

    (1978)
  • R. Cortese et al.

    J. Biol. Chem.

    (1976)
  • R.B. Wallace et al.

    Science

    (1980)
  • P.F. Johnson et al.

    Nature (London)

    (1983)
  • R.L. Lipnick et al.

    Biochemistry

    (1981)
  • R.E. Hurd et al.

    Nucleic Acids Res.

    (1977)
  • C.K. Chu et al.

    J. Org. Chem.

    (1976)
  • G. Habermehl et al.

    Justus Liebigs Ann. Chem.

    (1978)
  • D.M. Brown et al.

    J. Chem. Soc., Chem. Commun.

    (1981)
  • J.-L. Fourrey et al.

    J. Am. Chem. Soc.

    (1977)
  • R. Noyori et al.

    J. Am. Chem. Soc.

    (1978)
  • A.D. Argoudelis et al.

    J. Antibiot.

    (1976)
  • R.A. Earl et al.

    J. Heterocycl. Chem.

    (1977)
  • U. Reichman et al.

    J. Antibiot.

    (1977)
  • S.D. Bridges et al.

    J. Chem. Soc, Chem. Commun.

    (1977)
  • M.J. Robins et al.

    J. Chem. Soc., Chem. Commun.

    (1978)
  • A. Matsuda et al.

    J. Org. Chem.

    (1981)
  • K. Pankiewicz et al.

    J. Org. Chem.

    (1982)
  • U. Reichman et al.

    J. Heterocycl. Chem.

    (1976)
  • S.Y.-K. Tam et al.

    J. Org. Chem.

    (1979)
  • Cited by (279)

    View all citing articles on Scopus
    View full text