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J Am Chem Soc. 2011 Nov 30;133(47):19068-71. doi: 10.1021/ja209053b. Epub 2011 Nov 3.

Native chemical ligation of hydrolysis-resistant 3'-peptidyl-tRNA mimics.

Author information

1
Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Austria.

Abstract

Hydrolysis-resistant 3'-peptidyl-RNA conjugates that mimic tRNA termini represent a remarkable synthetic challenge, particularly if they contain amino acids with complex side-chain functionalities, such as arginines. Here we demonstrate a novel approach that combines solid-phase synthesis and bioconjugation to obtain these derivatives with high efficiency and purity. The key step is native chemical ligation of 3'-cysteinyl-RNA fragments to highly soluble peptide thioesters. The so-prepared 3'-peptidyl-RNA conjugates relate to resistance peptides that can render the ribosome resistant to macrolide antibiotics by a yet unknown ribosomal translation mechanism.

PMID:
22050598
DOI:
10.1021/ja209053b
[Indexed for MEDLINE]

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