Biomaterial Database

Synthesis of RNA 5'-Azides from 2'-O-Pivaloyloxymethyl-Protected RNAs and Their Reactivity in Azide-Alkyne Cycloaddition Reactions. 2017

Marcin Warminski, and Joanna Kowalska, and Jacek Jemielity

Division of Biophysics, Institute of Experimental Physics, Faculty of Physics, University of Warsaw , Pasteura 5, 02-093 Warsaw, Poland.

Commercially available 2'-O-pivaloyloxymethyl (PivOM) phosphoramidites were employed in an SPS protocol for RNA 5' azides. The utility of the N3-RNAs in CuAAC and SPAAC was demonstrated by RNA 5' labeling, chemical ligation including fragment joining and cyclization, and bioconjugation. As a result, several new RNA conjugates that may be valuable tools for studies on biological events such as innate immune response (cyclic dinucleotides), post-transcriptional gene regulation (circular RNAs), or mRNA turnover (m7G capped RNAs) were obtained.

UI	MeSH Term	Description	Entries
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003300	Copper	A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55.	Copper-63,Copper 63
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D000480	Alkynes	Hydrocarbons with at least one triple bond in the linear portion, of the general formula Cn-H2n-2.	Acetylenic Compounds,Alkyne,Acetylenes
D001386	Azides	Organic or inorganic compounds that contain the -N3 group.	Azide
D012313	RNA	A polynucleotide consisting essentially of chains with a repeating backbone of phosphate and ribose units to which nitrogenous bases are attached. RNA is unique among biological macromolecules in that it can encode genetic information, serve as an abundant structural component of cells, and also possesses catalytic activity. (Rieger et al., Glossary of Genetics: Classical and Molecular, 5th ed)	RNA, Non-Polyadenylated,Ribonucleic Acid,Gene Products, RNA,Non-Polyadenylated RNA,Acid, Ribonucleic,Non Polyadenylated RNA,RNA Gene Products,RNA, Non Polyadenylated
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D057930	Click Chemistry	Organic chemistry methodology that mimics the modular nature of various biosynthetic processes. It uses highly reliable and selective reactions designed to "click" i.e., rapidly join small modular units together in high yield, without offensive byproducts. In combination with COMBINATORIAL CHEMISTRY TECHNIQUES, it is used for the synthesis of new compounds and combinatorial libraries.	Click Chemical Reactions,Click Chemical Techniques,Chemical Reaction, Click,Chemical Reactions, Click,Chemical Technique, Click,Chemical Techniques, Click,Chemistries, Click,Chemistry, Click,Click Chemical Reaction,Click Chemical Technique,Click Chemistries,Reaction, Click Chemical,Reactions, Click Chemical,Technique, Click Chemical,Techniques, Click Chemical
D061565	Cycloaddition Reaction	Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products.	Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction