2002-35-9Relevant articles and documents
Quantitative LC–MS Provides No Evidence for m6dA or m4dC in the Genome of Mouse Embryonic Stem Cells and Tissues
Schiffers, Sarah,Ebert, Charlotte,Rahimoff, René,Kosmatchev, Olesea,Steinbacher, Jessica,Bohne, Alexandra-Viola,Spada, Fabio,Michalakis, Stylianos,Nickelsen, J?rg,Müller, Markus,Carell, Thomas
, p. 11268 - 11271 (2017)
Until recently, it was believed that the genomes of higher organisms contain, in addition to the four canonical DNA bases, only 5-methyl-dC (m5dC) as a modified base to control epigenetic processes. In recent years, this view has changed dramatically with the discovery of 5-hydroxymethyl-dC (hmdC), 5-formyl-dC (fdC), and 5-carboxy-dC (cadC) in DNA from stem cells and brain tissue. N6-methyldeoxyadenosine (m6dA) is the most recent base reported to be present in the genome of various eukaryotic organisms. This base, together with N4-methyldeoxycytidine (m4dC), was first reported to be a component of bacterial genomes. In this work, we investigated the levels and distribution of these potentially epigenetically relevant DNA bases by using a novel ultrasensitive UHPLC–MS method. We further report quantitative data for m5dC, hmdC, fdC, and cadC, but we were unable to detect either m4dC or m6dA in DNA isolated from mouse embryonic stem cells or brain and liver tissue, which calls into question their epigenetic relevance.
Nucleoside analogue as well as preparation method and application thereof
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Paragraph 0054; 0056; 0062; 0063; 0064; 0065, (2021/05/12)
The invention relates to a nucleoside analogue as well as a preparation method and application thereof, and belongs to the technical field of antiviral drugs. The nucleoside analogue disclosed by the invention is benzyl(((((2R,3S)-3-hydroxy-5-(6-(methylamino)-9H-purine-9-yl) tetrahydrofuran-2-yl) methoxy)(phenoxy) phosphoryl)-L-alaninate, and the structural formula of the nucleoside analogue is shown as a formula I in the specification. The nucleoside analogue disclosed by the invention is high in bioavailability, has anti-cancer and anti-virus effects, and can also improve the inherent immunity.
Oligodeoxynucleotides containing 2′-deoxy-1-methyladenosine and Dimroth rearrangement
Timofeev, Edward N.,Mikhailov, Sergey N.,Zuev, Andrei N.,Efimtseva, Ekaterina V.,Herdewijn, Piet,Somers, Robert L.,Lemaitre, Marc M.
, p. 928 - 937 (2008/02/04)
2′-Deoxy-1-methyladenosine was incorporated into synthetic oligonucleotides by phosphoramidite chemistry. Chloroacetyl protecting group and controlled anhydrous deprotection conditions were used to avoid Dimroth rearrangement. Hybridization studies of int
A Novel Route to N6-Alkylated 2′-Deoxyadenosine Using Benzotriazole as a Synthetic Auxiliary
El-Kafrawy, Sherif A.,Zahran, Magdy A.,Pedersen, Erik B.
, p. 280 - 283 (2007/10/03)
The N6-alkylation of 2′-deoxyadenosine is achieved by sodium borohydride reduction of the adduct formed from benzotriazole, an aliphatic, aromatic or heteroaromatic aldehyde and 2′-deoxyadenosine. In some cases ethoxy adducts are isolated and reduced to give the target N6-alkylated-2′-deoxyadenosine.
Synthesis of oligodeoxynucleotides containing 6-N-([13C]methyl)adenine and 2-N-([13C]methyl)guanine
Hofmann, Mechtild,Acedo, Montse,Fagan, Patricia,Wemmer, David,Eritja, Ramon,Diaz, Antonio R.
, p. 1825 - 1828 (2007/10/03)
Oligonucleotides containing 6-N-([l3C]methyl)adenine and 2-N-([13C]methyl)guanine have been prepared for NMR studies using the deprotection step to introduce the [13C]methylamine group. For this purpose, the use of 2′-deoxy-6-O-(pentafluorophenyl)inosine 1 and 2′-deoxy-2-fluoro-6-O-[2-(4-nitrophenyl)-ethyl]inosine 2 as precursors of the N-methylated nucleosides is described. Preliminary NMR characterization of the 13C-labelled oligonucleotides shows that the 13C chemical shift of the methyl group in N-methylguanine is sensitive to duplex formation, making it a useful local probe.
SYNTHESIS OF 2-DEOXY-β-D-RIBONUCLEOSIDES AND2,3-DIDEOXY.β-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL CELLS
Votruba, Ivan,Holy, Antonin,Dvorakova, Hana,Guenter, Jaroslav,Hockova, Dana,et al.
, p. 2303 - 2330 (2007/10/02)
Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs.All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series.Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety.The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom.On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives.Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed.The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-deoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-deoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.
Chemical Synthesis of Oligonucleotides Containing N6-Methyladenine Residues in the GATC Site
Guy, Andre,Molko, Didier,Wagrez, Laurence,Teoule, Robert
, p. 1034 - 1040 (2007/10/02)
To investigate by NMR the effects of adenine methylation, a set of oligodeoxynucleotides has been synthesized by phosphotriester or phosphoramidite procedures on silica-gel support.The preparation of fully protected 2'-deoxy-N6-methyladenosine
Methylation of Adenosine and Related Nucleosides with Trimethylselenonium Hydroxyde, and Regiospecific Effects of Copper(II) Ions
Yamauchi, Kiyoshi,Hattori, Kazue,Kinoshita, Masayoshi
, p. 1327 - 1330 (2007/10/02)
Methylation of adenosine, deoxyadenosine, 6-N-methyladenosine and 2'(3')-O-methyladenosines with trimethylselenonium hydroxyde was studied in the presence and absence of copper(II) acetylacetonate .It was found that copper(II) ions promoted methylation of the 2'(3')-OH groups of the ribonucleosides but suppressed methylation at the N-1 position of the adenine rings.The metal-ion effects are discussed in conjunction with a catalytic role for Cu(AA)2 in the reactions.
Methylation study of ribonucleosides, deoxyribonucleosides, and 2′-O-methylribonucleosides with trimethylsulphonium hydroxide and trimethylsulphonium iodide. Influence of the 2′-hydroxy-groups on the reactivity of the base moieties of ribonucleosides
Yamauchi, Kiyoshi,Nakagima, Toru,Kinoshita, Masayoshi
, p. 2787 - 2792 (2007/10/02)
Methylations of the naturally occuring ribonucleoside (1), deoxyribonucleoside (2), and 2′-O-methylribonucleoside (3) were carried out using trimethylsulphonium hydroxide (Me3SOH) and trimethylsulphonium iodide (Me3Sl). The base moiety of (2) and (3) are more reactive than the corresponding base moiety of (1). The sites and extent of methylation of (2) are considerably different from those of (1), but are almost identical with those of (3). The reactivities of (1)-(3) are discussed in connection to an intramolecular interaction of the 2′-OH groups with the base moiety of (1). The methylating characteristics of Me 3SOH and Me3Sl are also described. The kinetics indicate an SN2 mechanism for methylation of nucleosides by Me 3S+ ions.
