Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs

Maria Duca, David J. Maloney, Michiel Lodder, Bixun Wang, Sidney M. Hecht

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

Described herein is the preparation of new bisacylated tRNAs and their participation in protein synthesis. It has been reported that Thermus thermophilus phenylalanyl-tRNA synthetase can introduce two phenylalanine moieties onto the 3′-terminal adenosine of its cognate tRNA. It is also possible to prepare bisactivated tRNAs in vitro; these participate in protein synthesis [Wang, B.; Zhou, J.; Lodder, M.; Anderson, R. D.; Hecht, S. M. J. Biol. Chem. 2006, 281, 13865]. Presently, the chemical strategy used for the synthesis of the key intermediate bisacylated pdCpAs is described. Bis-S-alanyl- and bis-S-methionyl-pdCpAs were prepared initially. Further, S-threonine, S-allo-threonine, S-homoserine, and (S)-(+)-2-amino-3-hydroxy-3-methylbutyric acid were coupled with the dinucleotide to define preparative methods applicable to more complex amino acids bearing additional functionality in the form of an OH group.

Original languageEnglish (US)
Pages (from-to)4629-4642
Number of pages14
JournalBioorganic and Medicinal Chemistry
Volume15
Issue number13
DOIs
StatePublished - Jul 1 2007
Externally publishedYes

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Keywords

  • Aminoacylation
  • Enzymatic ligation
  • Hydroxylated amino acids
  • Protein synthesis
  • Transfer RNAs

ASJC Scopus subject areas

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

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