Total Synthesis of the Hypermodified tRNA Nucleoside Epoxyqueuosine

Queuosine is one of the most strongly modified nucleosides found in transferRNA (tRNA) of almost all species. Queuosine is found exclusively in the wooble position of the anticodon loop of several tRNA, where it is involved in tRNAAsp, tRNAAsn tRNAHis, and tRNATyr. The biosynthesis of queuosine is p...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-07, Vol.2013 (21), p.4483-4485
Main Authors: Thoma, Ines, Carell, Thomas
Format: Article
Language:English
Subjects:
Biosynthesis
Natural products
Nucleosides
Structure elucidation
Synthetic methods
tRNA
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Summary:Queuosine is one of the most strongly modified nucleosides found in transferRNA (tRNA) of almost all species. Queuosine is found exclusively in the wooble position of the anticodon loop of several tRNA, where it is involved in tRNAAsp, tRNAAsn tRNAHis, and tRNATyr. The biosynthesis of queuosine is performed by prokaryotes, and eukaryotes are fully dependent on this external source. To investigate the interesting biosynthesis of the Q base, we report here the first total synthesis of the direct biosynthetic precursor oQ. By using LC–MS in combination with special E. coli growing conditions (no vitamin B12 in the medium) we confirm the structure of the oQ natural products. The structure of the hypermodified nucleoside epoxyqueuosine (oQ), which is the biosynthetic precursor of queuosine (Q), was confirmed by total synthesis and HPLC–MS analysis of natural samples.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300586