A new bacterial adenosine-derived nucleoside as an example of RNA modification damage
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Abstract
The fields of RNA modification and RNA
damage both exhibit a plethora of non-canonical nucleo side structures. While RNA modifications have evolved
to improve RNA function, the term RNA damage
implies detrimental effects. Based on stable isotope
labelling and mass spectrometry, we report the identi fication and characterisation of 2-methylthio-1,N6-ethe noadenosine (ms2
ɛA), which is related to 1,N6-etheno adenine, a lesion resulting from exposure of nucleic
acids to alkylating chemicals in vivo. In contrast, a
sophisticated isoprene labelling scheme revealed that
ms2
ɛA biogenesis involves cleavage of a prenyl moiety in
the known transfer RNA (tRNA) modification 2-meth ylthio-N6-isopentenyladenosine (ms2
i
6
A). The relative
abundance of ms2
ɛA in tRNAs from translating ribo somes suggests reduced function in comparison to its
parent RNA modification, establishing the nature of the
new structure in a newly perceived overlap of the two
previously separate fields, namely an RNA modification
damage.
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Angewandte Chemie : International edition, 62, 11, Wiley-VCH, Weinheim, 2023, https://doi.org/10.1002/anie.202217128