17331-53-2Relevant articles and documents
Nucleotide libraries as a source of biologically relevant chemical diversity: Solution-phase synthesis
Zhou, Wenqiang,Upendran, Sathya,Roland, Arlene,Jin, Yi,Iyer, Radhakrishnan P.
, p. 1249 - 1252 (2000)
Solution-phase parallel synthesis of nucleotide library 1 consisting of 150 members is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
COMPOSITIONS AND METHODS FOR SYNTHESIS OF PHOSPHORYLATED MOLECULES
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Page/Page column 75, (2019/10/29)
The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.
Renewable amberlyst-15 catalyzed highly regioselective tritylation and deprotection of sugar-based diols
Valeru, Anil,Luo, Zhibin,Penjarla, Srishylum,Khan, Imran,Liu, Bin,Sngepu, Bhavanarushi,Xu, Yin,Xie, Jimin
, p. 318 - 326 (2018/10/15)
Amberlyst-15 catalyzed highly regioselective tritylation of sugar-based diols was achieved under mild condition using 4,4′-dimethoxytrityl alcohol (DMTrOH). Deprotection of the corresponding DMTr group was also established by the variation to protic solvent. Meanwhile, the heterogeneous catalyst Amberlyst-15 was recycled 3 times with satisfactory retention of catalytic activity and proved its potential application in industry.
In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues
Saudi, Milind,Zmurko, Joanna,Kaptein, Suzanne,Rozenski, Jef,Neyts, Johan,Van Aerschot, Arthur
, p. 98 - 109 (2014/03/21)
Several flaviviruses, such as the yellow fever virus and the dengue virus cause severe and potentially lethal infection in man. Following up on our initial hit 3′,5′-bistritylated uridine 1, a series of alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against dengue fever virus and yellow fever virus. Hereto, alkyl and aryl groups were attached at various positions of the sugar ring combined with subtle variation of the heterocyclic base. Among the new series of derivatives, 3′,5′-di-O-trityl-5-fluoro-2′-deoxyuridine (39) was the most efficient in this series and inhibited both yellow fever virus and dengue virus replication with a 50% effective concentration (EC50) of ～1 μg/mL without considerable cytotoxicity. The other fluorinated derivatives proved more toxic. Almost all diphenylmethylated pyrimidine nucleosides with 3′,5′-di-O-benzhydryl-2′-deoxyuridine (50) as the example were endowed with strong cytotoxic effects down to 1 μg/mL.
Tailoring peptide-nucleotide conjugates (PNCs) for nucleotide delivery in bacterial cells
De, Swarup,Groaz, Elisabetta,Herdewijn, Piet
, p. 2322 - 2348 (2014/04/17)
The design and synthesis of peptide-2′-deoxythymidine-5′-O- monophosphate conjugates as potential active delivery systems for nucleotides into auxotrophic E. coli strains is presented. A series of oligopeptides were allowed to react with 5′-O-(dibenzylphosphate)-2′-deoxythymidine or its suitably 3′-derivatized analogues to give the relevant peptide-nucleotide adducts, by the formation of a biolabile chemical connection. Using strategies based on the principles of orthogonal protection and activation, rational variations were made to the linker and the peptide moiety in order to tune the metabolic stability of the conjugates.
Exploring the potential of 3′-O-carboxy esters of thymidine as inhibitors of ribonuclease A and angiogenin
Ghosh, Kalyan S.,Debnath, Joy,Dutta, Palash,Sahoo, Bijaya K.,Dasgupta, Swagata
, p. 2819 - 2828 (2008/09/20)
In this study, compounds with a carboxy ester in lieu of the phosphate ester at the 3′-position have been employed to inhibit the ribonucleolytic activity of ribonuclease A (RNase A). Phosphates at the 3′-position of pyrimidine bases are well-known inhibitors of the protein. We have investigated the inhibition of RNase A by 3′-O-carboxy esters of thymidine. The compounds behave as competitive inhibitors with inhibition constants ranging from 42 to 95 μM. The mode of inhibition has also been confirmed by 1H NMR studies of the active site histidines of RNase A. Docking studies have further substantiated the experimental results. The compounds are also found to inhibit the ribonucleolytic activity of angiogenin, a homologous protein and potent inducer of blood vessel formation.
First synthesis of H-phosphonate oligonucleotides bearing N-unmodified bases
Wada, Takeshi,Honda, Fumio,Sato, Yuichi,Sekine, Mitsuo
, p. 915 - 918 (2007/10/03)
Oligodeoxyribonucleotides bearing H-phosphonate internucleotidic linkages and unmodified nucleobases were synthesized for the first time by the new H-phosphonate method using N-unprotected monomers. The 6-hydroxyhexyl phosphonates at both the 5' and 3' ends were found to be highly effective for stabilization of the H-phosphonate oligonucleotides. Solid-phase synthesis of H-phosphonate oligodeoxyribonucleotides containing dA, dC, dG, and T was achieved.
Regioselective acylation of 2'-deoxynucleosides through an enzymatic reaction with oxime esters
Gotor,Moris
, p. 626 - 628 (2007/10/02)
3'-O-Acyl derivatives of 2'-deoxynucleosides are obtained in good yield through an enzymatic reaction using oxime esters as acyl transfer agents.
SELF-COMPLEMENTARY TETRADEOXYRIBONUCLEOSIDE TRIPHOSPHATES. CONVENIENT CHEMICAL PREPARATION AND SPECTROSCOPIC STUDIES IN SOLUTION
Matsuzaki, Jun-ichi,Hotoda, Hitoshi,Sekine, Mitsuo,Hata, Tsujiaki,Higuchi, Shigesada,et al.
, p. 501 - 514 (2007/10/02)
Eight kinds of self-complementary tetradeoxyribonucleoside triphosphates were prepared by a simplified method which enabled us to omit purification of synthetic intermediates and provided the tetramers very rapidly and conveniently.The tetramers were characterized by enzyme assay and their conformations were studied by the use of UV and CD spectroscopic methods under various conditions.The detailed analysis of the CD spectra suggested that conformation of the tetramer duplexes was dependent on the sequence.
Simplified Liquid-Phase Preparation of Four Decadeoxyribonucleotides and their Preliminary Spectroscopic Characterization
Denny, William A.,Leupin, Werner,Kearns, David R.
, p. 2372 - 2393 (2007/10/02)
Four self-complementary decadeoxyribonucleotides, dApTpApTpApTpApTpApT,dApTpApTpCpGpApTpApT, dApTpApTpGpCpApTpApT and dApApApApApTpTpTpTpT, were chemically synthesized by the phosphotriester procedure.Efforts were concentrated on keeping the procedure as simple as possible, concomitant with obtaining high-purity products at each step of the process.The decamers were elaborated from the 3'-end, starting with a 3'-O-benzoylated monomer according to the scheme: monomer + monomer -> dimer + dimer -> tetramer + dimer -> hexamer + tetramer -> decamer.Putity of intermediates and of the fully blocked decamers were monitored by chromatography and by 300-MHz 1H-NMR. spectroscopy.The deblocked decadeoxyribonucleotides were characterized by their UV., CD., and 1H-NMR. spectra.
