Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 26, Pages 10645-10650Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003360
Keywords
artificial enzymes; cytokinins; N-6-isopentenyladenosine RNA; prenylation; RNA modifications
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Funding
- National Key RAMP
- D Program of China [2017YFA0208100, 2016YFA0602900, 2017YFD0201401]
- National Natural Science Foundation of China [91853124, 21977097, 21778057, 31672070, 21420102003, 31770398]
- Key Research Program of the Chinese Academy of Sciences [KFZD-SW-112]
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N-6-isopentenyladenosine (i(6)A) is an RNA modification found in cytokinins, which regulate plant growth/differentiation, and a subset of tRNAs, where it improves the efficiency and accuracy of translation. The installation and removal of this modification is mediated by prenyltransferases and cytokinin oxidases, and a chemical approach to selective deprenylation of i(6)A has not been developed. We show that a selected group of oxoammonium cations function as artificial deprenylases to promote highly selective deprenylation of i(6)A in nucleosides, oligonucleotides, and live cells. Importantly, other epigenetic modifications, amino acid residues, and natural products were not affected. Moreover, a significant phenotype difference in the Arabidopsis thaliana shoot and root development was observed with incubation of the cation. These results establish these small organic molecules as direct chemical regulators/artificial deprenylases of i(6)A.
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