3256-24-4

Upstream product

• 71933-65-8 C₆₆H₆₆ClN₈O₁₇P 
• 29886-19-9 2',3'-di-O-acetyladenosine 
• 60031-83-6 adenosine 5'-phosphoroimidazolidate sodium salt 
• 58-96-8 uridine 
• 61-19-8 5'-adenosine monophosphate 
• 1177254-60-2 5'-CUACUA-3' 
• 81246-79-9 5'-dimethoxytrityluridine 
• 75933-79-8 5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-uridine-3'-(4-chlorophenyl 5-chloro-8-quinolyl-phosphate) 
• 31505-87-0 6-N-benzoyl-2'-O-(tetrahyropyran-2-yl)adenosine 
• 129451-67-8 5'-O-dimethoxytrityluridine phosphoromorpholidite 

Downstream Products

• 606-02-0 uridine 2',3'-cyclic phosphate 
• 58-61-7 adenosine 
• 84-21-9 adenosine monophosphate 
• 130-49-4 adenosine 2'-monophosphate 
• 84-53-7 uridine-3'-phosphate 
• 131-83-9 uridine 2'-monophosphate 

Relevant academic research and scientific papers

A nucleotide dimer synthesis without protecting groups using montmorillonite as catalyst

A synthesis has been developed providing nucleotide dimers comprising natural or unnatural nucleoside residues. A ribonucleoside 5-phosphorimidazolide is added to a nucleoside adsorbed on montmorillonite at neutral pH with the absence of protecting groups. Approximately 30% of the imidazolide is converted into each 2-5 dimer and 3-5 dimer with the rest hydrolyzed to the 5-monophosphate. Experiments with many combinations have suggested the limits to which this method may be applied, including heterochiral and chimeric syntheses. This greener chemistry has enabled the synthesis of dimers from activated nucleotides themselves, activated nucleotides with nucleosides, and activated nucleotides with nucleotide 5-monophosphates.

Base moiety selectivity in cleavage of short oligoribonucleotides by di- and tri-nuclear Zn(II) complexes of azacrown-derived ligands

Cleavage of 6-mer oligoribonucleotides by the dinuclear Zn2+ complex of 1,3-bis[(1,5,9-triazacyclododecan-3-yl)oxymethyl]benzene (L 1) and the trinuclear Zn2+ complex of 1,3,5-tris[(1,5,9- triazacyclododecan-3-yl)oxymethyl

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.

Convenient Synthesis of Oligoribonucleotides Having 2'-5' and/or 3'-5' Phosphodiester Linkage

Sequence-defined oligoribonucleosides having 2'-5' and/or 3'-5' phosphodiester linkage have been synthesized by use of 5'-protected ribonucleoside 2',3'-cyclic phosphoramidite on solid support.In coupling reaction, pKa of azole as a catalyst governs the activation.The resulting 2'-5' and/or 3'-5' linked oligoribonucleotides were easily separated by reversed-phase chromatography.

CESIUM FLUORIDE PROMOTES SYNTHESYS OF RIBOOLIGONUCLEOTIDES VIA PHOSPHOTRIESTER APPROACH

In the presence of cesium fluoride, the reactions of a fully protected 5'-O-dimethoxytrityl-2'-O-tetrahydropyranyl-N-acylnucleoside 3'-(4-chlorophenyl, 5-chloro-8-quinolyl) phosphates with 5'-hydroxyl nucleosides proceeded rapidly under mild conditions to afford the corresponding ribonucleoside monophosphates in good yields.