21031-74-3Relevant academic research and scientific papers
A convenient, high-yield synthesis of 1-substituted uracil and thymine derivatives
Rejman, Dominik,Kova?ková, Soňa,Pohl, Radek,Dra?ínsky, Martin,Fiedler, Pavel,Rosenberg, Ivan
experimental part, p. 8513 - 8523 (2010/01/06)
Novel reagents for the synthesis of 1-substituted uracil and thymine derivatives have been developed. The aminolysis of 2- or 4-nitrophenyl 3-ethoxyacryloylcarbamate and 3-ethoxy-2-methylacryloylcarbamate with a variety of primary amino derivatives procee
Synthesis of carbocyclic pyrimidine nucleosides using the Mitsunobu reaction - Part I: Influence of the alcohol on N1- versus O2- alkylation
Ludek, Olaf R.,Meier, Chris
, p. 3145 - 3147 (2007/10/03)
The Mitsunobu reaction is an important tool in carbocyclic nucleoside chemistry for the direct coupling of alcohols with heterocyclic bases under mild conditions. Here, we report on the influence of the alcohol on the N1- vs. O2-alkylation of N
Photoreaction of Thymidine with Alkylamines. Application to Selective Removal of Thymine from DNA
Saito, Isao,Sugiyama, Hiroshi,Matsuura, Teruo
, p. 956 - 962 (2007/10/02)
A new type of photoreaction between thymidine (Thd) and alkylamines has been described.Irradiation of Thd and methylamine in NaHCO3 aqueous solution at 0 deg C provided ring-opened adduct 15 quantitatively, which on subsequent heating gave 1-methylthymine (8).High selectivity toward Thd has been observed when the photoreaction of a mixture of dAdo, dGyd, dGuo, and Thd with methylamine was carried out at 0 deg C in the presence of diazabicyclooctane (0.2 mM), and then the photolysate was kept at 20 deg C after irradiation.Irradiation of calf thymus DNA and methylamine under the specified conditions followed by heating at 70 deg C led to the efficient release of 8 from DNA.The extent of DNA modification is readily determined by the absorbance change at 300 nm, which corresponds to the amount of the ring-opened adduct between methylamine and thymine in DNA.Model experiments using thymidylyl(3'-5')-2'-deoxyadenosine demonstrate that the 3'-5' phosphodiester linkage is cleaved efficiently in this photoreaction.The present results indicate the irradiation of DNA with methylamine induces an exceedingly facile removal of thymine from DNA with the strand cleavage at the reacting thymine, providing a convenient and potentially useful method for thymine selective modification of DNA.
