A porphyrin C-nucleoside incorporated into DNA

Org Lett. 2002 Dec 12;4(25):4377-80. doi: 10.1021/ol0267376.

Abstract

[reaction: see text] A free porphyrin coupled on 2-deoxy-D-ribose was synthesized and incorporated into DNA via phosphoramidite chemistry. Substitution at the ends of a 5'-modified self-complementary duplex was found to be thermally and thermodynamically stabilizing. The porphyrin moiety strongly intercalates in the duplex when located near the center, and retains its fluorescence properties in DNA.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Base Sequence
  • Circular Dichroism
  • DNA / chemistry*
  • DNA / genetics
  • Fluorescence
  • Intercalating Agents / chemical synthesis*
  • Intercalating Agents / chemistry*
  • Molecular Structure
  • Nucleic Acid Conformation
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry*
  • Temperature
  • Thermodynamics

Substances

  • Intercalating Agents
  • Nucleosides
  • Porphyrins
  • porphyrin c
  • DNA