54898-05-4Relevant academic research and scientific papers
Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays Dedicated to Dr. Teruo Umemoto on the occasion of receiving the ACS Award for Creative Work in Fluorine Chemistry.
Shakhmin, Anton,Jones, John-Paul,Bychinskaya, Inessa,Zibinsky, Mikhail,Oertell, Keriann,Goodman, Myron F.,Prakash, G.K. Surya
, p. 226 - 230 (2015/03/05)
Analogs of ribonucleotides (RNA) stable to enzymatic hydrolysis were prepared and characterized. Computational investigations revealed that this class of compounds with a modified triphosphate exhibits the correct polarity and minimal steric effects compa
Design and synthesis of α-carboxy phosphononucleosides
Debarge, Sebastien,Balzarini, Jan,Maguire, Anita R.
experimental part, p. 105 - 126 (2011/04/17)
Rhodium catalyzed O-H insertion reactions employing α- diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5′-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.
Selective inhibitors of bacterial phosphopantothenoylcysteine synthetase
Patrone, James D.,Yao, Jiangwei,Scott, Nicole E.,Dotson, Garry D.
supporting information; experimental part, p. 16340 - 16341 (2010/01/30)
(Figure Presented) Bacterial phosphopantothenolycysteine synthetase (PPCS) catalyzes the formation of phosphopantothenoylcysteine (PPC) from (R)-phosphopantothenate, L-cysteine, and cytidine-5′-triphosphate (CTP) and has been shown to be essential for gro
Novel synthetic approach to multibenzoylated nucleosides
Zhu, Xue-Feng,Scott, A. Ian
, p. 1346 - 1354 (2008/09/19)
An improved and highly efficient synthetic approach to multibenzoylated nucleosides bearing free 5'-hydroxyl groups is described here. By employing t-butyldimethylsilyl (TBDMS) rather than the more commonly used dimethoxytrityl (DMTr) as a temporary 5'-OH
Phosphoramidate dinucleosides as hepatitis C virus polymerase inhibitors
Zlatev, Ivan,Dutartre, Hélène,Barvik, Ivan,Neyts, Johan,Canard, Bruno,Vasseur, Jean-Jacques,Alvarez, Karine,Morvan, Fran?ois
supporting information; experimental part, p. 5745 - 5757 (2009/09/29)
GC dinucleosides exhibiting a phosphoramidate internucleosidic linkage with neutral, amphiphile, positively or negatively charged side chains were synthesized. Their potential inhibitory effect on the hepatitis C virus (HCV) NS5B polymerase was evaluated
Synthesis, characterization, and biological properties of small branched RNA fragments containing chiral (Rp and Sp) 2′,5′-phosphorothioate linkages
Mourani, Rawan,Damha, Masad J.
, p. 203 - 229 (2007/10/03)
Synthetic branched RNA fragments were prepared to examine the stereochemical requirements for hydrolysis of RNA lariats by the yeast debranching enzyme (yDBR). Specifically, two branched trinucleoside diphosphates and a tetranucleoside triphosphate contai
Nucleotide sugars
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, (2008/06/13)
Phosphite linked nucleotide sugars, e.g. nucleoside-monophosphite-glycosides, are synthesized using phosphoramiditing agents. The success of the synthetic method is largely independent of the choice of sugar and of nucleotide. The phosphite linked nucleot
Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid
Cohen, Scott B.,Halcomb, Randall L.
, p. 6145 - 6152 (2007/10/03)
α-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of IS was a tetrazole-promoted coupling of a cytidine-5′-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for α-2,3-sialyltransferase. The Km of 1S was just 3-fold higher than that of 1, while the kcat of 1S was 2 orders of magnitude lower compared to 1.
The stability of trisubstituted internucleotide bond in the presence of the vicinal 2'-hydroxyl. Chemical synthesis of uridyl(2'-phosphate)-(3'-5')- uridine
Kierzek
, p. 1757 - 1768 (2007/10/02)
The effect of eleven different phosphoryl center protecting groups on the stability of trisubstituted internucleotide bond of the dimers (1a-k), in the presence of the vicinal 2'-hydroxyl, was examined. It has been found that electronic properties of the
