2. Academic Validation
  3. Chemical Deprenylation of N6 -Isopentenyladenosine (i6 A) RNA

Chemical Deprenylation of N6 -Isopentenyladenosine (i6 A) RNA

  • Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10645-10650. doi: 10.1002/anie.202003360.
Hou-Ping Cheng 1 2,  Xiao-Hui Yang 3,  Ling Lan 1 2,  Li-Jun Xie 1 2,  Chuan Chen 3,  Cuimei Liu 4,  Jinfang Chu 4 2,  Zhi-Yan Li 1,  Li Liu 1 2,  Tian-Qi Zhang 5,  Du-Qiang Luo 3,  Liang Cheng 1 2
Affiliations

Affiliations

  • 1 Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
  • 2 University of Chinese Academy of Sciences, Beijing, 100049, China.
  • 3 Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Life Science, Hebei University, Hebei, 071002, China.
  • 4 National Centre for Plant Gene Research (Beijing), Innovation Academy for Seed Design, Institute of Genetics and Developmental Biology, Chinese Academy of Sciences, Beijing, 100101, China.
  • 5 National Key Laboratory of Plant Molecular Genetics (NKLPMG), CAS Center for Excellence in Molecular Plant Sciences, Shanghai Institute of Plant Physiology and Ecology (SIPPE), Chinese Academy of Sciences, Shanghai, 200032, China.
PMID: 32198805 DOI: 10.1002/anie.202003360
Abstract

N6 -isopentenyladenosine (i6 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 i6 A has not been developed. We show that a selected group of oxoammonium cations function as artificial deprenylases to promote highly selective deprenylation of i6 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 i6 A.

Keywords

N6-isopentenyladenosine RNA; RNA modifications; artificial enzymes; cytokinins; prenylation.

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