3051-84-1

Usage

Uses

Used in Pharmaceutical Industry:
Uridine, adenylyl-(3'→5')is utilized as a therapeutic agent for its potential role in the treatment of cardiovascular diseases and neurological disorders. Its involvement in key biological processes makes it a candidate for interventions targeting these conditions.
Used in Research Applications:
In the scientific research field, Uridine, adenylyl-(3'→5')is employed as a tool for studying the mechanisms of RNA synthesis, gene expression, and cell signaling pathways, providing insights into the fundamental processes of life.
Used in Diagnostic Applications:
Uridine, adenylyl-(3'®5')may also be applied in diagnostic assays to evaluate the activity of enzymes involved in RNA metabolism or to detect abnormalities in RNA synthesis, which could be indicative of certain diseases or conditions.

Upstream product

• 99422-56-7 A(NBzl)-U 
• 74384-08-0 2',3'-O-Bis-diphenylphosphinothioyluridylyl(5'-3')-adenosine 
• 117686-69-8 C₇₅H₆₅ClN₇O₁₈P 
• 125444-59-9 2',3'-O-bis-diethylphosphinothioyluridylyl-(5'-3')-adenosine 
• 125444-61-3 2',3'-O-bis-di-n-butylphosphinothioyluridylyl-(5'-3')-adenosine 
• 29108-90-5 2',3'-di-O-acetyl-uridine 
• 35665-55-5 O^5'-acetyl-O^2'_,O3'-hydroxyphosphoryl-adenosine 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 74334-86-4 2',3'-O-Isopropylidene-5'-O-diphenylphosphinothioyluridine 
• 74334-87-5 Uridine-2',3',5'-O-tris-diphenylphosphinothioate 
• 634-01-5 adenosine 2',3'-cyclic monophosphate 
• 130-49-4 adenosine 2'-monophosphate 
• 58-96-8 uridine 
• 125456-06-6 2',3',5'-O-tris-di-n-butylphosphinothioyluridine 

Downstream Products

• 634-01-5 adenosine 2',3'-cyclic monophosphate 
• 58-96-8 uridine 
• 84-21-9 adenosine monophosphate 
• 130-49-4 adenosine 2'-monophosphate 

Relevant academic research and scientific papers

HIGH-YIELD SYNTHESIS OF OLIGORIBONUCLEOTIDES USING o-NITROBENZYL PROTECTION OF 2'-HYDROXYLS

Use of published procedures for photolytic removal of 2'-O-(o-nitrobenzyl) substituents from model oligoribonucleotides results in low yields of fully-deprotected products accompanied by significant amounts of oligomers carrying altered, ultraviolet light-resistant residues derived from the 2'-blocking groups.The efficiency of the deprotection has been found to be depend on pH; the side-reactions are avoided when the photolysis is carried out in solution buffered at pH 3.5.

Chemical synthesis of RNA via 2′-O-cyanoethylated intermediates

It was found that 2′-O-cyanoethyl group could be removed from 2′-O-cyanoethylated ribonucleoside derivatives by treatment with Bu4NF. This finding was successfully applied to the synthesis of oligoribonucleotides via their 2′-O-cyanoethylated derivatives as key intermediates where a cyanoethyl group was used as the 2′-hydroxyl protecting group. The rate of condensation using this protecting group in the presence of various activators was generally faster than that observed when a TBDMS group was used as the protecting group.

Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

The comparative rates of acid-catalysed removal often 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined. The Royal Society of Chemistry 2000.

Synthesis of 1'%,2',3',4'%,5',5"-(2)H6-β-D-ribonucleosides and 1'%,2',2",3',4'%,5',5"-(2)H7-β-D-2'-deoxyribonucleosides for Selective Suppression of Proton Resonances in Partially-deuterated Oligo-DNA, Oligo-RNA and in 2,5A core ((1)H-NMR window)

Raney nickel-(2)H2O exchange reaction on an epimeric mixture of methyl α/β-D-ribofuranoside 1 produced methyl 1%,2,3,4%,5,5'-(2)H6-α/β-D-ribofuranoside 2 ( >97 atom percent (2)H at C2, C3, C5/5'; ca. 85 atom percent (2)H at C4(C4%); ca. 20 atom percent (2)H at C1(C1%)) which was obtained in 60 - 80percent yield along with epimeric xylo and arabino by-products.Toluoylation of the crude 2 in dry pyridine and a careful separation on a column of silica gel gave pure 1-O-methyl-2,3,5-tri-O-(4-toluoyl)-α/β-D-1%,2,3,4%,5,5'-(2)H6-ribofuranoside 4 (48percent).Conversion of 4 to1-O-acetyl-2,3,5-tri-O-toluoyl-α/β-D-1%,2,3,4%,5,5'-(2)H6-ribofuranoside 6 (82percent) provided the crucial building block for the synthesis of deuterionucleosides for RNA or DNA synthesis.Compound 6 was then condensed with silyated uracil, N4-benzoylcytosine, N6-benzoyladenine, N2-acetyl-O6-diphenylcarbamoylguanine and thymine in anhydrous solvent using trimethylsilyl trifluoromethanesulfonate to give the corresponding isomerically pure 1'%,2',3',4'%,5',5"-(2)H6-ribonucleoside derivatives 7, 8, 9, 10, 11 in 75, 85, 60, 73 and 91percent yields, respectively. 1'%,2',3',4'%,5',5"-(2)H6-ribonucleosides 13-16 were converted in high yields to the corresponding 1'%,2',2",3',4'%,5',5"-(2)H7-2'-deoxynucleosides 41-44 in the following manner: 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TPDS)-1'%,2',3',4'%,5',5"-(2)H6-nucleosides 29-32 were converted to the corresponding 2'-O-phenoxythiocarbonyl derivatives 33-36, which were deoxygenated by tri-n-butyltin deuteride to give 1'%,2',2",3',4'%,5',5"-(2)H7-2'-deoxynucleosides 37-40 and subsequently deprotected to give 41-44.Pure 1'%,2',3',4'%,5',5"-(2)H6-ribonucleoside derivatives 12-15, 1'%,2',2",3',4'%,5',5"-(2)H7-2'-deoxynucleoside blocks 41-44 and their natural-abundance counterparts were then used to assemble partially deuterated ribonucleotide-dimers (* indicates deuterated moiety): UpA* 77, CpG* 78, ApU* 79, GpC* 80, partially deuterated 2'-deoxyribonucleotide-dimers d(TpA*) 93, d(CpG*) 94, d(ApT*) 95, d(GpC*) 96 and partially deuterated 2,5A core (A*2'p5'A2'p5'A*) (109).These nine partially deuterated oligonucleotides were subsequently compared with their corresponding natural-abundance counterparts by 500 MHz (1)H-NMR spectroscopy to evaluate the actual NMR simplifications achieved in the non-deuterated part ((1)H-NMR window) as a result of specific deuterium incorporation.Detailed 1D (1)H-NMR (500 MHz), 2D correlation spectra (DQF-COSY and TOCSY), T1 measurements for (1)H-, (13)C- and INEPT (13)C-NMR spectra have been presented and discussed to assess the utility of stereospecific deuterium incorporation to create the (1)H- or (13)C-NMR window.

An Improved Method for the Application of the 4-Methoxybenzyl Group to Protect the 2'-Hydroxyl Group in the Ribonucleotide Synthesis by TFA-acidolysis

The cleavage of the 4-methoxybenzyl group from the 2'-OH-position of ribonucleosides by the hydrogenation with different Pd-catalysts as well as trifluoroacetic acid has been studied in detail.During hydrogenation, side reactions at the base residue of cytidine occurred which, however, could be extensively suppressed by PdCl2 catalysis.More practicable results were obtained with trifluoroacetic acid in the presence of cation scavengers, allowing smoothly to convert a series of 2'-methoxybenzyl ribonucleotides to the homogeneous deprotection products.

Formation of Inter-nucleotide Bond: Use of Diphenylphosphinothioyl Group as a Protective Group

A convenient method for the preparation of oligonucleotides using diphenylphosphinothioyl group as the protective group for 5'-OH of the ribose moiety of nucleoside is described.The dinucleotides, uridyl (5',3')-adenosine and adenylyl (5',3')-adenosine have been prepared employing this reagent.