Synthesis and structure elucidation of the human tRNA nucleoside mannosyl-queuosine

Markus Hillmeier, Mirko Wagner, Timm Ensfelder, Eva Korytiakova, Peter Thumbs, Markus Müller and Thomas Carell ()
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Markus Hillmeier: Ludwig-Maximilians-Universität München
Mirko Wagner: Ludwig-Maximilians-Universität München
Timm Ensfelder: Ludwig-Maximilians-Universität München
Eva Korytiakova: Ludwig-Maximilians-Universität München
Peter Thumbs: Ludwig-Maximilians-Universität München
Markus Müller: Ludwig-Maximilians-Universität München
Thomas Carell: Ludwig-Maximilians-Universität München

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Queuosine (Q) is a structurally complex, non‐canonical RNA nucleoside. It is present in many eukaryotic and bacterial species, where it is part of the anticodon loop of certain tRNAs. In higher vertebrates, including humans, two further modified queuosine-derivatives exist ‐ galactosyl‐ (galQ) and mannosyl-queuosine (manQ). The function of these low abundant hypermodified RNA nucleosides remains unknown. While the structure of galQ was elucidated and confirmed by total synthesis, the reported structure of manQ still awaits confirmation. By combining total synthesis and LC-MS-co-injection experiments, together with a metabolic feeding study of labelled hexoses, we show here that the natural compound manQ isolated from mouse liver deviates from the literature-reported structure. Our data show that manQ features an α‐allyl connectivity of its sugar moiety. The yet unidentified glycosylases that attach galactose and mannose to the Q‐base therefore have a maximally different constitutional connectivity preference. Knowing the correct structure of manQ will now pave the way towards further elucidation of its biological function.

Date: 2021
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DOI: 10.1038/s41467-021-27371-9

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