243657-07-0Relevant articles and documents
Phototriggers for nucleobases with improved photochemical properties
Furuta, Toshiaki,Watanabe, Takayoshi,Tanabe, Satoshi,Sakyo, Jun,Matsuba, Chie
, p. 4717 - 4720 (2007)
(Chemical Equation Presented) Synthesis and photochemical properties of new photoremovable protecting groups for nucleobases are described. Four caged 2′-deoxycytidines (dCs) were synthesized, and their photochemical properties were measured under simulat
Photocleavable protecting groups as nucleobase protections allowed the solid-phase synthesis of base-sensitive SATE-prooligonucleotides
Alvarez, Karine,Vasseur, Jean-Jacques,Beltran, Thierry,Imbach, Jean-Louis
, p. 6319 - 6328 (2007/10/03)
The first synthesis of oligodeoxynucleotide heteropolymers carrying base-sensitive S-pivaloylthioethyl (t-Bu-SATE) phosphotriester linkages has been performed. It is based on the use of 6-nitroveratryloxycarbonyl (NVOC) and 2,2'-bis(2-nitrophenyl)ethoxycarbonyl (diNPEOC) groups as nucleobase protections in combination with photolysis deprotection. The synthesis was realized using the phosphoramidite approach on solid support bearing a 1-(o- nitrophenyl)-1,3-propanediol linker. The removal of the protecting groups and the cleavage of the oligonucleotides from the solid support were accomplished in a single photolysis procedure upon UV irradiation at wavelengths > 300 nm. Faster deprotection rates were observed for diNPEOC-protected nucleosides and oligomers than with NVOC-protected ones. The synthesis of pentanucleoside t- Bu-SATE-phosphotriesters d((5')TpCpCpCpTp(3')), d((5')TpApApApAp(3')), and d((5')TpGpGpGpTp(3')) and of dodecanucleoside t-Bu-SATE-phosphotriesters and -phosphorothioate d((5')ApCpApCpCpCpApApTpTpCpTp(3')) and d((5')ApGpApApTpTpGpGpGpTpGpTp(3')) demonstrated the efficiency of the method.
