An unnatural hydrophobic base, 4-propynylpyrrole-2-carbaldehyde, as an efficient pairing partner of 9-methylimidazo[(4,5)-b]pyridine.

Bioorg Med Chem Lett

Research Center for Advanced Science and Technology, The University of Tokyo, Komaba, Meguro-ku, Tokyo 4-6-1 153-8904, Japan.

Published: December 2003

AI Article Synopsis

  • Researchers designed and synthesized a new nucleoside derivative called Pa' to create unnatural base pairs for DNA replication.
  • The pairing of Pa' with a partner named Q was compared to an earlier pair (Pa and Q) to assess improvements in stability and incorporation into DNA.
  • Enhanced thermal stability and incorporation efficiency of the new Q-Pa' pair were achieved due to increased hydrophobicity and stacking stability from the propynyl group's addition, aiding the goal of expanding the genetic alphabet.

Article Abstract

To develop unnatural base pairs that function in replication, we designed 4-propynylpyrrole-2-carbaldehyde (designated as Pa') and synthesized the nucleoside derivatives of Pa'. The base pairing of Pa' with the partner, 9-methylimidazo[(4,5)-b]pyridine (Q), was compared to that of pyrrole-2-carbaldehyde (Pa), which was previously developed as a specific pairing partner of Q. The thermal stability of a DNA duplex containing the Q-Pa' pair and the incorporation efficiency of the Pa' substrate (dPa'TP) into DNA opposite Q by the Klenow fragment of Escherichia coli DNA polymerase I were improved, in comparison with those of the Q-Pa pair. These improvements result from the increased hydrophobicity and stacking stability of Pa' by the introduction of the propynyl group to Pa, providing valuable information for the further development of unnatural base pairs toward the expansion of the genetic alphabet.

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Source
http://dx.doi.org/10.1016/j.bmcl.2003.09.059DOI Listing

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