50408-20-3Relevant articles and documents
Bismethylene triphosphate nucleotides of uridine 4-phosphate analogues: A new class of anionic pyrimidine nucleotide analogues
Taylor, Scott D.,Mirzaei, Farzad,Bearne, Stephen L.
, p. 1403 - 1412 (2008/09/17)
(Chemical Equation Presented) Cytidine-5′-triphosphate synthase (CTPS) catalyzes the formation of cytidine triphosphate (CTP) from glutamine, uridine 5′-triphosphate (UTP), and adenosine 5′-triphosphate (ATP). This reaction proceeds via formation of the high-energy intermediate UTP-4-phosphate (UTP-4-P). Stable analogues of UTP-4-P may be potent inhibitors of CTPS and useful as lead structures for the development of anticancer and antiviral agents. Several bismethylene triphosphate (BMT) nucleotides of uridine 4-phosphate (U-4-P) analogues have been prepared. A key step was the selective methanolysis, with the aid of a tin catalyst, of the 5′ ester moiety of 2′,3′,5′-tri-O-acetyl or tri-O-benzoyl U-4-P analogues. We believe this represents the first general approach to the selective cleavage of 5′ benzoyl esters in benzoylated nucleosides. Mitsunobu coupling of these 5′-deprotected U-4-P analogues to an unsymmetrical, protected BMT bearing a free phosphonic acid moiety at one of the terminal positions gave fully protected BMT-U-4-P analogues. Global deprotection of these species was achieved using TMSBr followed by treatment with NH4OH-MeOH or NH 4OH-pyridine. The resulting BMT nucleotides represent a new class of anionic pyrimidine nucleotide analogues.
Durenesulfonic Acid Derivatives as New Condensing Reagents in the Nucleotide Synthesis Following the Triester Method
Losse, Guenter,Stang, Norbert
, p. 19 - 24 (2007/10/02)
As shown by the synthesis of a series of ribonucleotide blocks durenesulfonyl chloride/1-methylimidazole and 1-(3-durenylsulfonyloxy)-6-nitrobenzotriazole (15) are adventageous alternative condensing reagents for the triester method.Hereby the 2'-OH function of the ribose is protected by the 4-methoxybenzyl group, which can be removed suitably by dry TFA/anisole instead of trityl tetrafluoroborate.
Synthesis of 2',3'-Differentiated Ribonucleosides via Glycosylation. Reactions with 2-O-Me or 2-O-TBDMS Ribofuranose Derivatives. 1. Pyrimidine Series
Chavis, C.,Dumont, F.,Wightman, R. H.,Ziegler, J. C.,Imbach, J. L.
, p. 202 - 206 (2007/10/02)
The synthesis of 2',3' asymmetrically substituted pyrimidine ribonucleosides in 70-95percent yields by using modified Vorbruggen conditions with "nonparticipating" 2-O-CH3 and 2-O-TBDMS ribofuranoses is described.Such compounds are useful synthons for oligoribonucleotide synthesis, including incorporation of "rare" bases.New and practically useful conditions for placement (using 1,2,4-triazole) and removal (KF/crown ether) of the tert-butyldimethylsilyl (TBDMS) protecting group are also reported.