Total Synthesis of the Hypermodified tRNA Nucleoside Epoxyqueuosine

European Journal of Organic Chemistry, 2013, DOI: 10.1002/ejoc.201300586, Volume 2013, Issue 21, pages 4483–4485 published on 07.06.2013

European Journal of Organic Chemistry, online article

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.  

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