» Articles » PMID: 35226025

Conjugation of RNA 2'-OH Acylation: Mechanisms Determining Nucleotide Reactivity

Overview
Specialty Chemistry
Date 2022 Feb 28
PMID 35226025
Authors
Affiliations
Soon will be listed here.
Abstract

The acylation reactivity of RNA 2'-OH groups has proven broadly useful for labeling and mapping RNA. Here we perform kinetics studies to test the mechanisms governing this reaction, and we find strong steric and inductive effects modulating reactivity. The results shed light on new strategies for improved conjugation and mapping.

Citing Articles

Site-Selective Modification and Labeling of Native RNA.

Kha T, Zhao Y, Zhu R Chemistry. 2025; 31(12):e202404244.

PMID: 39865772 PMC: 11855268. DOI: 10.1002/chem.202404244.


Spontaneous base flipping helps drive Nsp15's preferences in double stranded RNA substrates.

Wright Z, Butay K, Krahn J, Wilson I, Gabel S, DeRose E Nat Commun. 2025; 16(1):391.

PMID: 39755678 PMC: 11700208. DOI: 10.1038/s41467-024-55682-0.


Chemical diversity of reagents that modify RNA 2'-OH in water: a review.

Shioi R, Kool E Chem Sci. 2024; .

PMID: 39309104 PMC: 11412305. DOI: 10.1039/d4sc05317f.


Second-Generation Chiral Amino Acid Derivatives Afford High Stereoselectivity and Stability in Aqueous RNA Acylation.

Shioi R, Chatterjee S, Xiao L, Zhong W, Kool E J Org Chem. 2024; 89(11):8055-8063.

PMID: 38809698 PMC: 11898221. DOI: 10.1021/acs.joc.4c00686.


Selective Arylation of RNA 2'-OH Groups via SAr Reaction with Trialkylammonium Heterocycles.

Chatterjee S, Xiao L, Zhong W, Feng S, Kool E Angew Chem Int Ed Engl. 2024; 63(25):e202403496.

PMID: 38625814 PMC: 11905364. DOI: 10.1002/anie.202403496.


References
1.
Brown R, Andrews C, Elcock A . Stacking Free Energies of All DNA and RNA Nucleoside Pairs and Dinucleoside-Monophosphates Computed Using Recently Revised AMBER Parameters and Compared with Experiment. J Chem Theory Comput. 2015; 11(5):2315-28. PMC: 4651843. DOI: 10.1021/ct501170h. View

2.
Xiao L, Fang L, Kool E . Acylation probing of "generic" RNA libraries reveals critical influence of loop constraints on reactivity. Cell Chem Biol. 2022; 29(8):1341-1352.e8. PMC: 9391288. DOI: 10.1016/j.chembiol.2022.05.005. View

3.
Paredes E, Evans M, Das S . RNA labeling, conjugation and ligation. Methods. 2011; 54(2):251-9. DOI: 10.1016/j.ymeth.2011.02.008. View

4.
Velema W, Kietrys A, Kool E . RNA Control by Photoreversible Acylation. J Am Chem Soc. 2018; 140(10):3491-3495. PMC: 6486827. DOI: 10.1021/jacs.7b12408. View

5.
Lima S, Hildenbrand J, Korostelev A, Hattman S, Li H . Crystal structure of an RNA helix recognized by a zinc-finger protein: an 18-bp duplex at 1.6 A resolution. RNA. 2002; 8(7):924-32. PMC: 1370309. DOI: 10.1017/s1355838202028893. View