Misacylated Transfer RNAs Having a Chemically Removable Protecting Group

Michiel Lodder, Serguei Golovine, Andrei L. Laikhter, Vladimir A. Karginov, Sidney M. Hecht

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

The 4-pentenoyl group and a number of derivatives have been studied as protecting groups for Nα of the aminoacyl moiety in misacylated tRNAs. The unsubstituted 4-pentenoyl group itself was found to function as efficiently as any of the derivatives studied. Four different N-(4-pentenoyl)aminoacyl-tRNACUAS were prepared and shown to undergo deprotection readily upon admixture of aqueous iodine; the derived misacylated tRNAs all functioned well as suppressors of a nonsense codon in an in vitro protein biosynthesizing system. Also prepared were four Nα-(4-pentenoyl)-aspartyl-tRNACUAS that were protected on the side chain carboxylate as the nitroveratryl ester. Following treatment with aqueous iodine, the misacylated suppressor tRNAs incorporated the aspartate derivatives into position 27 of dihydrofolate reductase by suppression of a UAG codon in the mRNA. The suppression yields were significantly better than those obtained when side chain protection was absent. The resulting "caged proteins" were inactive, but full catalytic potential was restored by irradiation under conditions sufficient to effect deprotection of the side chain carboxylate moiety.

Original languageEnglish (US)
Pages (from-to)794-803
Number of pages10
JournalJournal of Organic Chemistry
Volume63
Issue number3
DOIs
StatePublished - Feb 6 1998
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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