40615-37-0Relevant academic research and scientific papers
Alternatives to the 4,4′-dimethoxytrityl (DMTr) protecting group
Reese, Colin B.,Yan, Hongbin
, p. 2567 - 2570 (2004)
The 9-phenyl- and the 9-(p-tolyl)-xanthen-9-yl groups 2a and 2b are recommended as alternatives to the 4,4′-dimethoxytrityl group 1 for the protection of the 5′-hydroxy functions in oligonucleotide synthesis.
Indications of 5′ to 3′ Interbase Electron Transfer as the First Step of Pyrimidine Dimer Formation Probed by a Dinucleotide Analog
Jian, Yajun,Maximowitsch, Egle,Liu, Degang,Adhikari, Surya,Li, Lei,Domratcheva, Tatiana
, p. 7526 - 7537 (2017)
Pyrimidine dimers are the most common DNA lesions generated under UV radiation. To reveal the molecular mechanisms behind their formation, it is of significance to reveal the roles of each pyrimidine residue. We thus replaced the 5′-pyrimidine residue wit
AN EFFICIENT PROCEDURE FOR THE SOLID PHASE TRITYLATION OF NUCLEOSIDES AND NUCLEOTIDES
Reddy, M. P.,Rampal, J. B.,Beaucage, S. L.
, p. 23 - 26 (1987)
The interaction of tetra-n-butylammonium perchlorate with dimethoxytrityl chloride in the presence of 2,4,6-collidine in dichloromethane permitted a rapid and high yield tritylation of nucleosides or nucleotides covalently attached to a solid support.
LINKAGE MODIFIED OLIGOMERIC COMPOUNDS
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Page/Page column 78, (2020/01/11)
The present invention provides gapped oligomeric compounds comprising from 1 to about 3 internucleoside linkages having one of formulas I to XVI. In certain embodiments, inclusion of from 1 to about 3 internucleoside linkages of one of formulas I to XVI,
Synthesis and biological evaluation of triazolyl 13α-estrone-nucleoside bioconjugates
Bodnár, Brigitta,Mernyák, Erzsébet,W?lfling, János,Schneider, Gyula,Herman, Bianka Edina,Szécsi, Mihály,Sinka, Izabella,Zupkó, István,Kupihár, Zoltán,Kovács, Lajos
, (2016/09/23)
2' -Deoxynucleoside conjugates of 13α-estrone were synthesized by applying the copper-catalyzed alkyne-azide click reaction (CuAAC). For the introduction of the azido group the 5? -position of the nucleosides and a propargyl ether functional group on the 3-hydroxy group of 13α-estrone were chosen. The best yields were realized in our hands when the 3? -hydroxy groups of the nucleosides were protected by acetyl groups and the 5? -hydroxy groups were modified by the tosyl-azide exchange method. The commonly used conditions for click reaction between the protected-5? -azidonucleosides and the steroid alkyne was slightly modified by using 1.5 equivalent of Cu(I) catalyst. All the prepared conjugates were evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cell lines (HeLa, MCF-7 and A2780) and the potential inhibitory activity of the new conjugates on human 17β-hydroxysteroid dehydrogenase 1 (17β-HSD1) was investigated via in vitro radiosubstrate incubation. Some protected conjugates displayed moderate antiproliferative properties against a panel of human adherent cancer cell lines (the protected cytidine conjugate proved to be the most potent with IC50 value of 9 μM). The thymidine conjugate displayed considerable 17β-HSD1 inhibitory activity (IC50 = 19 μM).
Synthesis of covalently linked parallel and antiparallel DNA duplexes containing the metal-mediated base pairs T-Hg(ii)-T and C-Ag(i)-C
Ono, Takashi,Yoshida, Kyohei,Saotome, Yuko,Sakabe, Rei,Okamoto, Itaru,Ono, Akira
supporting information; experimental part, p. 1542 - 1544 (2011/03/22)
DNA duplexes fixed in anti-parallel and parallel orientations by introducing covalent linkages have been synthesized and metal ions, Hg(ii) and Ag(i), were incorporated into pyrimidine-pyrimidine base pairs.
A divalent metal-dependent self-cleaving DNAzyme with a tyrosine side chain
Lam, Curtis H.,Hipolito, Christopher J.,Hollenstein, Marcel,Perrin, David M.
supporting information; experimental part, p. 6949 - 6954 (2011/11/05)
The enzymatic incorporation of a phenol-modified 2′-deoxyuridine triphosphate gave rise to a modified DNA library that was subsequently used in an in vitro selection for ribophosphodiester-cleaving DNAzymes in the presence of divalent zinc and magnesium cations. After 11 rounds of selection, cloning and sequencing resulted in 14 distinct sequences, the most active of which was Dz11-17PheO. Dz11-17PheO self-cleaved an embedded ribocytidine with an observed rate constant of 0.20 ± 0.02 min-1 in the presence of 10 mM Mg2+ and 1 mM Zn2+ at room temperature. The activity was inhibited at low concentrations of Hg2+ cations and somewhat higher concentrations of Eu3+ cations.
Synthesis of oligodeoxynucleotides using fully protected Deoxynucleoside 3c-Phosphoramidite building blocks and base recognition of Oligodeoxynucleotides incorporating N3-Cyano-Ethylthymine
Tsunoda, Hirosuke,Kudo, Tomomi,Ohkubo, Akihiro,Seio, Kohji,Sekine, Mitsuo
experimental part, p. 7509 - 7531 (2011/02/28)
Oligodeoxynucleotide (ODN) synthesis, which avoids the formation of side products, is of great importance to biochemistry-based technology development. One side reaction of ODN synthesis is the cyanoethylation of the nucleobases. We suppressed this reaction by synthesizing ODNs using fully protected deoxynucleoside 3c-phosphoramidite building blocks, where the remaining reactive nucleobase residues were completely protected with acyl-, diacyl-, and acyl-oxyethylene-type groups. The detailed analysis of cyanoethylation at the nucleobase site showed that N3-protection of the thymine base efficiently suppressed the Michael addition of acrylonitrile. An ODN incorporating N3-cyanoethylthymine was synthesized using the phosphoramidite method, and primer extension reactions involving this ODN template were examined. As a result, the modified thymine produced has been proven to serve as a chain terminator.
RIBONUCLEIC ACID COMPOUND AND METHOD OF LIQUID-PHASE SYNTHESIS OF OLIGONUCLEIC ACID COMPOUND
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Page/Page column 16, (2010/11/24)
A novel phosphotriesterified ribonucleic acid compound which is important for liquid-phase synthesis of oligo-RNA is provided. Examples of the ribonucleic acid compound of the invention may include ribonucleic acid compounds represented by the following general formula: (wherein B represents adenine, guanine, cytosine or uracil or a modified form thereof; R21 represents aryl which may be substituted or a monocyclic or bicyclic heterocyclic group which may be substituted; R20 represents H or alkyl which may be substituted; and R1 represents a protecting group which can be removed at 90% or more at a temperature in the range from 0°C to 60°C under acidic conditions at a pH value from 2 to 4 within 24 hours).
Study on reactivity and protection of the α-hydroxyphosphonate moiety in 5′-nucleotide analogues: Formation of the 3′-O-P-C(OH)-C4′ internucleotide linkage
Kralikova, Sarka,Masojidkova, Milena,Budesinsky, Milos,Rosenberg, Ivan
, p. 329 - 347 (2007/10/03)
The recently described epimeric nucleosidyl-5′-C-phosphonates (α-hydroxyphos-phonates) represent novel nucleotide analogues that can be incorporated into chimeric oligonucleotides by the phosphotriester condensation method. In order to prepare suitable protected monomer(s) we have studied condensation reaction between protected 2′-deoxythymidine and 2′-deoxythymidinyl-5′-C-phosphonate, both as model compounds, in dependence on the nature of the 5′-hydroxyl protecting group. We have found that the O-acetyl group is unstable in the presence of TPSCl or MSNT used as condensing agents for activation of the phosphorus moiety. This instability negatively influences the scope of the condensation process. On the other hand, introduction of the O-methoxycarbonyl group gave excellent results. The O-methoxycarbonyl group does not participate in the condensation process, and its quantitative introduction into the nucleotide analogues is accomplished using a novel acylating agent, methoxycarbonyl tetrazole.
