Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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

Fingerprint

Transfer RNA
Threonine
Phenylalanine-tRNA Ligase
Bearings (structural)
Homoserine
Thermus thermophilus
Phenylalanine
Adenosine
Proteins
Amino Acids
5'-phospho-2'-deoxyribocytidylylriboadenosine

Keywords

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

ASJC Scopus subject areas

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

Cite this

Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs. / Duca, Maria; Maloney, David J.; Lodder, Michiel; Wang, Bixun; Hecht, Sidney.

In: Bioorganic and Medicinal Chemistry, Vol. 15, No. 13, 01.07.2007, p. 4629-4642.

Research output: Contribution to journalArticle

Duca, Maria ; Maloney, David J. ; Lodder, Michiel ; Wang, Bixun ; Hecht, Sidney. / Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs. In: Bioorganic and Medicinal Chemistry. 2007 ; Vol. 15, No. 13. pp. 4629-4642.
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