Copying Life: Synthesis of an Enzymatically Active Mirror-Image DNA-Ligase Made of D-Amino Acids

Cell Chem Biol. 2019 May 16;26(5):645-651.e3. doi: 10.1016/j.chembiol.2019.02.008. Epub 2019 Mar 14.

Abstract

Our objective is the creation of a mirror-image synthetic biology: that is, to mimic, entirely independent of Nature, a biological system and to re-create it from artificial component parts. Utilizing enantiomeric L-nucleotides and D-amino acids rather than the natural components, we use chemical synthesis toward a basic, self-replicating mirror-image biological system. Here, we report the synthesis of a functional DNA-ligase in the D-enantiomeric conformation, which is an exact mirror-image of the natural enzyme, exhibiting DNA ligation activity on chirally inverted nucleic acids in L-conformation, but not acting on natural substrates and with natural co-factors. Starting from the known structure of the Paramecium bursaria chlorella virus 1 DNA-ligase and the homologous but shorter DNA-ligase of Haemophilus influenza, we designed and synthesized chemically peptides, which could then be assembled into a full-length molecule yielding a functional protein. The structure and the activity of the mirror-image ligase were characterized, documenting its enantiospecific functionality.

Keywords: D-protein; DNA ligase; enantiomeric molecules; orthogonal biology; synthetic biology.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemistry
  • Amino Acids / metabolism*
  • Bacterial Proteins / chemistry
  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism*
  • Circular Dichroism
  • DNA Ligases / chemistry
  • DNA Ligases / genetics
  • DNA Ligases / metabolism*
  • Haemophilus influenzae / enzymology
  • Paramecium / virology
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Protein Structure, Tertiary
  • Recombinant Proteins / biosynthesis
  • Recombinant Proteins / genetics
  • Stereoisomerism
  • Viral Proteins

Substances

  • Amino Acids
  • Bacterial Proteins
  • Peptides
  • Recombinant Proteins
  • Viral Proteins
  • Chlorella virus DNA ligase
  • DNA Ligases
  • DNA ligase (NAD)