94189-75-0Relevant academic research and scientific papers
Design and synthesis of dephosphono dna analogues containing 1,2,3-triazole linker and their uv-melting studies with DNA/RNA
Madhuri, Vangala,Kumar, Vaijayanti A.
scheme or table, p. 97 - 111 (2012/07/13)
This article describes the synthesis of 3/5 linked 1,2,3-triazolyl dithymidine derivatives, their incorporation into oligonucleotides, and evaluation of their thermal stabilities toward complementary DNA/RNA. Copyright Taylor and Francis Group, LLC.
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
scheme or table, 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.
Synthesis of 3'O-(2-cyanoethyl)-2'-deoxythymidine-5'-phosphate as a model compound for evaluation of Cyanoethyl Cleavage
Keller, Angelika C.,Serva, Saulius,Knapp, Diana C.,Kwiatkowski, Marek,Engels, Joachim W.
experimental part, p. 515 - 534 (2010/02/28)
An essential and challenging task during the development of our sequencing-by-synthesis (SBS) technique is the evaluation of efficient cyanoethyl (CE) cleavage conditions. For this purpose 3'-O-(2-cyanoethyl)-2'- deoxythymidine-5'-phosphate as a model compound as well as a short DNA oligomer bearing the CE function as terminal group were synthesized and used for various deprotection experiments. As it is already known for 2'-O-CE-protected RNA oligonucleotides, the CE function can be cleaved with tetrabutylammonium fluoride (TBAF) in THF. Indeed, by using 3'-O-(2-cyanoethyl)-2'-deoxythymidine- 5'-phosphate as a simple model compound for cleavage tests, we found out that the 3'-O-CE function is quantitatively cleaved with 1 m TBAF in THF. However, the CE group is also cleaved by other small bases like hydroxy groups under alkaline conditions. The CE cleavage with TBAF in THF gives the fastest and quantitative removal of the CE group under mild conditions for our sequencing-by-synthesis (SBS) application. The efficient removal of the 3'-CE group is crucial for the proof-of-principle of our SBS approach using dye-labeled 3'-CE-blocked dNTPs, which is currently under investigation. Herein we describe the application of 3'-O-(2-cyanoethyl)-2'-deoxythymidine-5'- phosphate as model compound for the development of reversible terminators for the SBS technique. Furthermore we suggest that nucleoside phosphates bearing any removable 3'-modification might be suitable model compounds for cleavage studies in a heterogeneous environment comparable to an oligonucleotide/aprotic solvent system.
An improved transient method for the synthesis of N-benzoylated nucleosides
Zhu, Xue-Feng,Williams Jr., Howard J.,Scott, A. Ian
, p. 1233 - 1243 (2007/10/03)
The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCl) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.
New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation
Maguire, Anita R.,Hladezuk, Isabelle,Ford, Alan
, p. 369 - 372 (2007/10/03)
An improved procedure for the synthesis of N-benzoyl-2′,3′-O-isopropylidene uridine via one-step selective N-benzoylation of 2′,3′-O-isopropylidene uridine has been developed. An efficient synthetic route to N-benzoyl thymidine via initial tribenzoylation, followed by selective hydrolysis of the benzoates is also described. De-N-benzoylation of N-benzoylated thymidine and uridine derivatives can be conveniently effected under neutral conditions, by heating with benzyl alcohol.
A NEW CLASS OF CONDENSING REAGENTS FOR RAPID INTERNUCLEOTIDE BOND FORMATION IN THE PHOSPHOTRIESTER APPROACH AND PREPARATION OF N3-BENZOYLTHYMIDINE AS A KEY INTERMEDIATE IN OLIGODEOXYRIBONUCLEOTIDE SYNTHESIS
Matsuzaki, Jun-ichi,Hotoda, Hitoshi,Sekine, Mitsuo,Hata, Tujiaki
, p. 4019 - 4022 (2007/10/02)
Rapid internucleotide bond formation in the phosphotriester approach has been achieved in high yield by use of bis(2,4,6-trihalophenyl)phosphorochloridates (TCP and TBP) as new condensing reagents and the benzoyl group as the N3-imide protecting group of thymidine.
