Chemical Deprenylation of N6‐Isopentenyladenosine (i6A) RNA. Issue 26 (27th May 2020)

• Record Type: Journal Article
• Authors: Cheng, Hou‐Ping; Yang, Xiao‐Hui; Lan, Ling; Xie, Li‐Jun; Chen, Chuan; Liu, Cuimei; Chu, Jinfang; Li, Zhi‐Yan; Liu, Li; Zhang, Tian‐Qi; Luo, Du‐Qiang; Cheng, Liang
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 26(2020)
• Page Start: 10645
• Page End: 10650
• Publication Date: 2020-05-27
• Subjects: artificial enzymes -- cytokinins -- N6-isopentenyladenosine RNA -- prenylation -- RNA modifications; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202003360
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Artificial Deprenylase : An oxoammonium cation has been identified as a unique chemical motif that targets prenylated i 6 A RNA and exhibits remarkable selectivity and efficiency in both live cells and plants. This demonstrates that small organic molecules as artificial enzyme mimics can be powerful tools to modulate RNA epigenetic modification for the precise control of biological events.