Dal Magro, Christina, Keller, Patrick, Kotter, Annika, Werner, Stephan, Duarte, Victor, Marchand, Virginie ORCID: 0000-0002-8537-1139, Ignarski, Michael ORCID: 0000-0001-6057-7694, Freiwald, Anja, Mueller, Roman-Ulrich, Dieterich, Christoph, Motorin, Yuri, Butter, Falk ORCID: 0000-0002-7197-7279, Atta, Mohamed and Helm, Mark ORCID: 0000-0002-0154-0928 (2018). A Vastly Increased Chemical Variety of RNA Modifications Containing a Thioacetal Structure. Angew. Chem.-Int. Edit., 57 (26). S. 7893 - 7898. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

Recently discovered new chemical entities in RNA modifications have involved surprising functional groups that enlarge the chemical space of RNA. Using LC-MS, we found over 100 signals of RNA constituents that contained a ribose moiety in tRNAs from E. coli. Feeding experiments with variegated stable isotope labeled compounds identified 37 compounds that are new structures of RNA modifications. One structure was elucidated by deuterium exchange and high-resolution mass spectrometry. The structure of msms(2)i(6)A (2-methylthiomeihylenethio-N6-isopentenyl-adenosine) was confirmed by methione-D3 feeding experiments and by synthesis of the nucleobase. The mssms(2)i(6)Acontains a thioacetal, shown in vitro to be biosynthetically derived from ms(2)i(6)A by the radical-SAM enzyme MiaB. This enzyme performs thiomethylation, forming ms(2)i(6)A from i(6)A in a first turnover. The new thioacetal is formed by a second turnover. Along with the pool of 36 new modifications, this work describes a new layer of RNA modification chemistry.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Dal Magro, ChristinaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Keller, PatrickUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Kotter, AnnikaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Werner, StephanUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Duarte, VictorUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Marchand, VirginieUNSPECIFIEDorcid.org/0000-0002-8537-1139UNSPECIFIED
Ignarski, MichaelUNSPECIFIEDorcid.org/0000-0001-6057-7694UNSPECIFIED
Freiwald, AnjaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Mueller, Roman-UlrichUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Dieterich, ChristophUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Motorin, YuriUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Butter, FalkUNSPECIFIEDorcid.org/0000-0002-7197-7279UNSPECIFIED
Atta, MohamedUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Helm, MarkUNSPECIFIEDorcid.org/0000-0002-0154-0928UNSPECIFIED
URN: urn:nbn:de:hbz:38-182598
DOI: 10.1002/anie.201713188
Journal or Publication Title: Angew. Chem.-Int. Edit.
Volume: 57
Number: 26
Page Range: S. 7893 - 7898
Date: 2018
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1521-3773
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
PROTON-MAGNETIC-RESONANCE; TRANSFER-RIBONUCLEIC-ACID; EXPERIMENTAL ASSIGNMENT; RADICAL-SAM; IDENTIFICATION; METHYLTHIOTRANSFERASES; SEPARATION; CLUSTERS; POSITION; PURINEMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/18259

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