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Synthesis and testing of new modified nucleosides.

M E Jung1, C J Nichols, O Kretschik

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA.

Nucleosides & Nucleotides
|August 5, 1999
PubMed
Summary

Researchers developed efficient synthesis routes for novel modified nucleosides. This includes D- and L-enantiomers of methylene-expanded oxetanocin isonucleosides and L-2

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Nucleoside Analog Synthesis

Background:

  • Modified nucleosides are crucial in antiviral and anticancer therapies.
  • Existing synthetic routes often lack efficiency or broad applicability.
  • Development of enantiomerically pure nucleoside analogs is essential for targeted drug design.

Purpose of the Study:

  • To establish novel, high-yielding synthetic pathways for diverse modified nucleosides.
  • To synthesize specific classes of isonucleosides, including methylene-expanded and dideoxy analogs.
  • To prepare enantiomerically pure L-ribose and 2-deoxy-L-ribose derivatives and their corresponding nucleosides.

Main Methods:

  • Development of new synthetic methodologies for nucleoside analog construction.
  • Stereoselective synthesis to obtain both D- and L-enantiomers.
  • Preparation of oxa and thia analogues of dideoxy isonucleosides.

Main Results:

  • Successfully synthesized D- and L-enantiomers of methylene-expanded oxetanocin isonucleosides (1a-c).
  • Prepared L-2',3'-dideoxy isonucleosides (2abc), including oxa and thia variants.
  • Established new routes for L-ribose (3a) and 2-deoxy-L-ribose (3b), and their modified nucleosides (4).

Conclusions:

  • The developed routes offer efficient and high-yielding access to valuable modified nucleosides.
  • This work expands the toolkit for synthesizing enantiomerically pure nucleoside analogs.
  • The synthesized compounds hold potential for further investigation in medicinal chemistry.

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