2382-66-3Relevant academic research and scientific papers
Efficient synthesis of N4-methyl-and N4- hydroxycytidine phosphoramidites
Lu, Jun,Li, Nan-Sheng,Koo, Selene C.,Piccirilli, Joseph A.
body text, p. 2708 - 2712 (2010/10/21)
Nucleotide analogues empower chemical biologists to investigate the relationship between RNA structure and function on a level deeper than would be possible using only the four natural nucleotides. N4-Methylcytidine and N4-hydroxycytidine represent two cytidine analogues whose physicochemical properties enable biochemical tests for specific aspects of cytidine function within RNA. Here, we describe an efficient synthesis of N 4-methylcytidine and N4-hydroxycytidine derivatives, and their corresponding phosphoramidites in 40.7% and 25.2% yield, respectively, starting from uridine. These phosphoramidites couple efficiently during solid-phase synthesis, although N4-hydroxycytidine reverts partially to cytidine (5-10%) during oligonucleotide synthesis and deprotection. Georg Thieme Verlag Stuttgart.
Base moiety selectivity in cleavage of short oligoribonucleotides by di- and tri-nuclear Zn(II) complexes of azacrown-derived ligands
Laine, Maarit,Ketomaeki, Kaisa,Poijaervi-Virta, Paeivi,Loennberg, Harri
experimental part, p. 2780 - 2787 (2009/09/07)
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 RNA using 2′-O-DTM protection
Semenyuk, Andrey,Foeldesi, Andras,Johansson, Tommy,Estmer-Nilsson, Camilla,Blomgren, Peter,Braennvall, Mathias,Kirsebom, Leif A.,Kwiatkowski, Marek
, p. 12356 - 12357 (2007/10/03)
tert-Butyldithiomethyl (DTM), a novel hydroxyl protecting group, cleavable under reductive conditions, was developed and applied for the protection of 2′-OH during solid-phase RNA synthesis. This function is compatible with all standard protecting groups used in oligonucleotide synthesis, and allows for fast and high-yield synthesis of RNA. Oligonucleotides containing the 2′-O-DTM groups can be easily deprotected under the mildest possible aqueous and homogeneous conditions. The preserved 5′-O-DMTr function can be used for high-throughput cartridge RNA purification. Copyright
An Improved Method for the Application of the 4-Methoxybenzyl Group to Protect the 2'-Hydroxyl Group in the Ribonucleotide Synthesis by TFA-acidolysis
Losse, G.,Pechstein, Birgit
, p. 46 - 54 (2007/10/02)
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.
4-CHLOROPHENYL 5-CHLORO-8-QUINOLYL PHOSPHOROCHLORIDATE: A PRACTICALLY USEFUL PHOSPHORYLATING AGENT FOR OLIGORIBONUCLEOTIDE SYNTHESIS VIA PHOSPHOTRIESTER APPROACH
Takaku, Hiroshi,Yoshida, Masatoshi,Kamaike, Kazuo,Hata, Tsujiaki
, p. 197 - 200 (2007/10/02)
5'-O-Dimethoxytrityl-2'-O-tetrahydropyranylnucleosides (2) smoothly reacts with 4-chlorophenyl 5-chloro-8-quinolyl phosphorochloridate (1) prepared form 4-chlorophenyl phosphodichloridate and 5-chloro-8-hydroxyquinoline to give 5'-O-dimethoxytrityl-2'-O-tetrahydropyranylnucleoside 3'-(4-chlorophenyl, 5-chloro-8-quinolyl) phosphates (3) in high yields.They are key intermediates for the synthesis of oligoribonucleotides via phosphotriester approach.
The chemical synthesis of oligoribonucleotides. IX. A comparison of protecting groups in the dichloridite procedure
Ogilvie, Kelvin K.,Theriault, Nicole Y.,Seifert, Jan-Marcus,Pon, Richard T.,Nemer, Mona J.
, p. 2686 - 2693 (2007/10/02)
A series of phosphorodichloridites has been prepared incorporating the most commonly used phosphate protecting groups in oligonucleotide synthesis.The groups incude trichloroethyl, tribromoethyl, cyanoethyl, benzyl, methyl, p-chlorophenyl, and nitrophenetyl.The trichloroethyl and the nitrophenethyl appear to be the most stable groups while the cyanoethyl and methyl offer specific advantages.The benzyl and p-chlorophenyl groups are subject to limitations on their utility.Condensations can be carried out in a range of solvents incuding THF, pyridine, and DMF and at temperatures from -78 deg C to 20 deg C with a slight drop in yield with increasing temperature, at least for dinucleotide condensations.
