title: Native chemical ligation of hydrolysis-resistant 3'-peptidyl-tRNA mimics.
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.
authors: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Austria.
authors: Anna-Skrollan
authors: AS
authors: Geiermann
authors: Norbert
authors: N
authors: Polacek
authors: Ronald
authors: R
authors: Micura
mesh_terms: D006868:Hydrolysis; D008968:Molecular Conformation; D018716:Molecular Mimicry; D012346:RNA, Transfer, Amino Acyl / Q000737:chemistry*
chemical_list: D012346:RNA, Transfer, Amino Acyl; C019037:tRNA, peptidyl-