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Series GSE247565 Query DataSets for GSE247565
Status Public on Nov 14, 2023
Title Stereoselective RNA Reaction with Chiral 2'-OH Acylating Agents
Organism synthetic construct
Experiment type Other
Summary The reactivity of RNA 2'-OH groups with acylating agents has recently been investigated for high-yield conjugation of RNA strands. To date, only achiral molecules have been studied for this reaction, despite the complex chiral structure of RNA. Here we prepare a set of chiral acylimidazoles and study their stereoselectivity in RNA reactions. Reactions performed with unfolded and folded RNAs reveal that positional selectivity and reactivity vary widely with local RNA macro-chirality. We further document remarkable effects of chirality on reagent reactivity, identifying an asymmetric reagent with 1000-fold greater reactivity than prior achiral reagents. In addition, we identify a chiral compound with higher RNA structural selectivity than any previously reported RNA-mapping species. Further, azide-containing homologs of a chiral dimethylalanine reagent were synthesized and applied to local RNA labeling, displaying 92% yield and 16:1 diastereoselectivity. The results establish that reagent stereochemistry and chiral RNA structure are critical elements of small molecule-RNA reactions, and demonstrate new chemical strategies for selective RNA modification and probing.
Overall design 10 samples are analyzed, including replicates for each conditions: (1) A-case RNA library treated with 50mM S1; (2) A-case RNA library treated with 50mM R1; (3) A-case RNA library treated with 100µM S2; (4) A-case RNA library treated with 100µM R2;(5) A-case RNA library treated DMSO (as control); (6) U-case RNA library treated with 50mM S1; (7) U-case RNA library treated with 50mM R1; (8) U-case RNA library treated with 100µM S2; (9) U-case RNA library treated with 100µM R2;(10) U-case RNA library treated DMSO (as control);
Contributor(s) Shioi R, Xiao L, Chatterjee S, Kool ET
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Submission date Nov 13, 2023
Last update date Nov 14, 2023
Contact name Lu Xiao
Organization name Stanford University
Street address 369 N-S Axis, Stauffer I, 109
City Stanford
State/province California
ZIP/Postal code 94305
Country USA
Platforms (1)
GPL26697 HiSeq X Ten (synthetic construct)
Samples (10)
GSM7892987 A-S1
GSM7892988 A-R1
GSM7892989 A-S2
BioProject PRJNA1039745

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Supplementary file Size Download File type/resource
GSE247565_R-score_chiral_molecules.xlsx 61.1 Kb (ftp)(http) XLSX
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Raw data are available in SRA

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