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Electrophilic RNA for Peptidyl-RNA Synthesis and Site-Specific Cross-Linking with tRNA-Binding Enzymes.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2016 Oct 17; Vol. 55 (43), pp. 13553-13557. Date of Electronic Publication: 2016 Sep 26. - Publication Year :
- 2016
-
Abstract
- RNA functionalization is challenging due to the instability of RNA and the limited range of available enzymatic reactions. We developed a strategy based on solid phase synthesis and post-functionalization to introduce an electrophilic site at the 3' end of tRNA analogues. The squarate diester used as an electrophile enabled sequential amidation and provided asymmetric squaramides with high selectivity. The squaramate-RNAs specifically reacted with the lysine of UDP-MurNAc-pentapeptide, a peptidoglycan precursor used by the aminoacyl-transferase FemX <subscript>Wv</subscript> for synthesis of the bacterial cell wall. The peptidyl-RNA obtained with squaramate-RNA and unprotected UDP-MurNAc-pentapeptide efficiently inhibited FemX <subscript>Wv</subscript> . The squaramate unit also promoted specific cross-linking of RNA to the catalytic Lys of FemX <subscript>Wv</subscript> but not to related transferases recognizing different aminoacyl-tRNAs. Thus, squaramate-RNAs provide specificity for cross-linking with defined groups in complex biomolecules due to its unique reactivity.<br /> (© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Aminoacyltransferases chemistry
Cross-Linking Reagents chemistry
Models, Molecular
Molecular Conformation
Peptides chemistry
RNA chemistry
RNA, Transfer chemistry
Uridine Diphosphate N-Acetylmuramic Acid chemistry
Uridine Diphosphate N-Acetylmuramic Acid metabolism
Aminoacyltransferases metabolism
Cross-Linking Reagents metabolism
Peptides metabolism
RNA biosynthesis
RNA, Transfer metabolism
Uridine Diphosphate N-Acetylmuramic Acid analogs & derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 55
- Issue :
- 43
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 27667506
- Full Text :
- https://doi.org/10.1002/anie.201606843