55798-09-9Relevant 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.
, 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.
Glycoconjugates, products of uridine derivatives phosphitylation and oxidation as glycosyltransferases potential inhibitors
Grec, Marta,Swierk, Piotr,Pastuch, Gabriela,Szeja, Wieslaw
, p. 652 - 663 (2011/06/19)
The title compounds, variously protected 5′-uridine derivatives connected with 1-thiosugar with thiophosphoesters fragment (17-22) were synthesized in sequence of reactions: phosphitylation - reaction of 5′-hydroxyl group of selectively protected nucleoside with a phosphitylating agent (N,N-diisopropyl chlorophosphoamidite), connection an phosphoroamidites with 2-bromoethanol or 3-bromopropanol and secondary oxidation with sulfur presence and finally condensation reaction of obtained products with 1-thiosugar. Received glycoconjugates (17-22) had a structure which mimic to structure of natural glycosyltransferases substrates.
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
Preparation and cleavage reactions of 3′-thiouridylyl-(3′→5′)-uridine
Liu, Xiaohai,Reese, Colin B.
, p. 2227 - 2236 (2007/10/03)
3′-Thiouridylyl-(3′→5′)-uridine [(Us)pU] 3 is prepared by coupling together the disulfide 14 and the 5′-H-phosphonate 18, and then removing the protecting groups. (Us)pU 3 readily undergoes cleavage in 0.05 mol dm-3 sodium glycinate buffer (pH 10.06) at 50 °C to give, in the first instance, uridine 4 and 3′-thiouridine 2′,3′-cyclic phosphorothioate 21; in glacial acetic acid at 30 °C, it rapidly undergoes cleavage in essentially the same way. The behaviour of (Us)pU 3 is compared with that of uridylyl-(3′→5′)-uridine (UPU) 1a under the same basic and acidic reaction conditions. (Us)pU 3 and 3′-thiouridine 2′,3′-cyclic phosphorothioate 21 are both substrates for ribonuclease A; (Us)pU 3 is a substrate for Crotalus adamanteus snake venom phosphodiesterase but not for calf spleen phosphodiesterase.
