Synthesis of conformationally restricted dinucleotides by ring-closing metathesis

Org Lett. 2000 Dec 28;2(26):4217-9. doi: 10.1021/ol0067639.

Abstract

[reaction:see text] The ring-closing metathesis reaction has been used in the synthesis of conformationally restricted dinucleotides as well as a 3'-nucleotide analogue. From bis-allylic nucleoside phosphates obtained from simple nucleoside precursors, the synthesis of unsaturated cyclophosphates has been accomplished using either Grubbs' catalyst or an improved analogue. Hereby, the conformational freedom of the nucleic acid phosphordiester linkage has been efficiently constrained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Nucleic Acid Conformation
  • Nucleotides / chemical synthesis*
  • Nucleotides / chemistry

Substances

  • Nucleotides