Synthesis of aspartic acid derivatives useful for the preparation of misacylated transfer RNAs

M. Lodder, C. F. Crasto, A. L. Laikhter, H. An, T. Arslan, V. A. Karginov, G. F. Short, S. M. Hecht

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

Several derivatives of aspartic acid were protected on Nα as their NVOC derivatives, and on the side chain carboxylates as nitroveratryl esters. Following activation as the cyanomethyl esters, these fully protected aspartate derivatives were converted to the respective pdCpA esters. The protected aspartyl-pdCpA esters were then utilized as substrates for T4 RNA ligase in the presence of in vitro transcripts of tRNA lacking the pCpA dinucleotide normally found at the 3'-end. In this fashion, several misacylated tRNAs were prepared; following photolytic deprotection, these were employed successfully for incorporation into proteins at predetermined positions.

Original languageEnglish (US)
Pages (from-to)884-891
Number of pages8
JournalCanadian Journal of Chemistry
Volume78
Issue number6
DOIs
StatePublished - Jan 1 2000
Externally publishedYes

Keywords

  • Amino acid protection
  • Aminoacylated nucleotides
  • Protein synthesis
  • TRNA activation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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  • Cite this

    Lodder, M., Crasto, C. F., Laikhter, A. L., An, H., Arslan, T., Karginov, V. A., Short, G. F., & Hecht, S. M. (2000). Synthesis of aspartic acid derivatives useful for the preparation of misacylated transfer RNAs. Canadian Journal of Chemistry, 78(6), 884-891. https://doi.org/10.1139/v99-246