Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives

Bioorg Med Chem. 2012 Apr 15;20(8):2679-89. doi: 10.1016/j.bmc.2012.02.024. Epub 2012 Feb 15.


N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thiothreonine were incorporated into a predetermined position of a catalytically competent dihydrofolate reductase (DHFR) analogue lacking cysteine, and the elaborated proteins were derivatized site-specifically at the thiothreonine residue with a fluorophore.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Dinucleoside Phosphates / chemical synthesis*
  • Dinucleoside Phosphates / chemistry
  • Dinucleoside Phosphates / metabolism*
  • Molecular Structure
  • RNA, Transfer / chemistry
  • RNA, Transfer / metabolism*
  • Stereoisomerism
  • Threonine / analogs & derivatives*
  • Threonine / chemistry*
  • Transfer RNA Aminoacylation


  • Dinucleoside Phosphates
  • 5'-phospho-2'-deoxyribocytidylylriboadenosine
  • Threonine
  • RNA, Transfer