Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives

Shengxi Chen, Nour Eddine Fahmi, Ryan C. Nangreave, Youcef Mehellou, Sidney Hecht

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2679-2689
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number8
DOIs
StatePublished - Apr 15 2012

Keywords

  • Aminoacylation
  • Fluorescence labeling
  • Protein synthesis
  • Sulfur-containing amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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