201420-61-3Relevant academic research and scientific papers
Design and synthesis of α-carboxy phosphononucleosides
Debarge, Sebastien,Balzarini, Jan,Maguire, Anita R.
, 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.
Decoding the logic of the tRNA regiospecificity of nonribosomal femX Wv aminoacyl transferase www.angewandte.org
Fonvielle, Matthieu,Chemama, Maryline,Lecerf, Maxime,Villet, Regis,Busca, Patricia,Bouhss, Ahmed,Etheve-Quelquejeu, Melanie,Arthur, Michel
supporting information; experimental part, p. 5115 - 5119 (2010/11/04)
Natural selection: Replacement of the 3′-OH group of Ala-tRNA Ala with 3′-H affected FemXWv-catalyzed aminoacyl transfer from the 2 -position, but not substrate binding. The ability of FemXWv to bind and transacylate the 3′-O-Ala isomer initially formed by alanyl-tRNA synthetase (AlaRS) may be crucial for efficient competition with the ribosome (see scheme). (Figure Presented).
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
Stereo- And Regioselective Introduction of 1- or 2-Hydroxyethyl Group via Intramolecular Radical Cyclization Reaction with a Novel Silicon-Containing Tether. An Efficient Synthesis of 4′α-Branched 2′-Deoxyadenosines
Shuto, Satoshi,Kanazaki, Makiko,Ichikawa, Satoshi,Minakawa, Noriaki,Matsuda, Akira
, p. 746 - 754 (2007/10/03)
An efficient method for the synthesis of 4′α-branched 2′-deoxyadenosines starting from 2′-deoxyadenosine has been developed utilizing a novel radical cyclization reaction with a silicon tether. The radical reaction of 4′β-(phenylseleno)-3′-O-diphenylvinylsilyl adeninenucleoside derivative 17 with Bu3SnH and AIBN, followed by Tamao oxidation, gave selectively either the 4′α-(2-hydroxyethyl) derivative 21 or 4′α-(1-hydroxyethyl) derivative 19, depending on the reaction conditions. With a lower Bu3SnH concentration, the reaction gave the 4′α-(2-hydroxyethyl) derivative 21, via a 6-endo-radical cyclized product 20, as the sole product in 72% yield. The reaction of 17 in the presence of excess Bu3SnH gave 19 quantitatively, via a 5-exo-cyclized product 18, as a diastereomeric mixture. The reaction mechanism was examined using Bu3SnD. The results demonstrated that the 5-exo cyclized (3-oxa-2-silacyclopentyl)methyl radical (C) was formed initially which was trapped when the concentration of Bu3SnH(D) was high enough. With lower concentrations of Bu3SnHCD), radical C rearranged into the ring-enlarged 4-oxa-3-silacyclohexyl radical (D) which was then trapped with Bu3SnH(D) to give endo-cyclized product F.
