Expanded Genetic Alphabets: Managing Nucleotides That Lack Tautomeric, Protonated, or Deprotonated Versions Complementary to Natural Nucleotides

ACS Synth Biol. 2017 Feb 17;6(2):194-200. doi: 10.1021/acssynbio.6b00193. Epub 2016 Oct 7.

Abstract

2,4-Diaminopyrimidine (trivially K) and imidazo[1,2-a]-1,3,5-triazine-2(8H)-4(3H)-dione (trivially X) form a nucleobase pair with Watson-Crick geometry as part of an artificially expanded genetic information system (AEGIS). Neither K nor X can form a Watson-Crick pair with any natural nucleobase. Further, neither K nor X has an accessible tautomeric form or a protonated/deprotonated state that can form a Watson-Crick pair with any natural nucleobase. In vitro experiments show how DNA polymerase I from E. coli manages replication of DNA templates with one K:X pair, but fails with templates containing two adjacent K:X pairs. In analogous in vivo experiments, E. coli lacking dKTP/dXTP cannot rescue chloramphenicol resistance from a plasmid containing two adjacent K:X pairs. These studies identify bacteria able to serve as selection environments for engineering cells that replicate AEGIS pairs that lack forms that are Watson-Crick complementary to any natural nucleobase.

Keywords: DNA; artificially expanded genetic information systems (AEGIS); in vivo conversion; polymerases; synthetic biology.

MeSH terms

  • Base Pairing / genetics
  • DNA / genetics
  • DNA Polymerase I / metabolism
  • DNA Replication / genetics
  • Escherichia coli / genetics
  • Nucleotides / genetics*
  • Pyrimidines / metabolism

Substances

  • Nucleotides
  • Pyrimidines
  • 2,4-diaminopyrimidine
  • DNA
  • DNA Polymerase I