Oligoribonucleotide synthesis by the use of 1-(2-cyanoethoxy)ethyl (CEE) as a 2'-hydroxy protecting group.
A novel method for the synthesis of oligoribonucleotides has been developed by the use of 1-(2-cyanoethoxy)ethyl (CEE) as a 2'-hydroxy protecting group. The CEE group was introduced to the 2'-position of an N-acyl-3',5'-O-silyl protected ribonucleoside under acidic conditions. A combination of the use of N-acyl and 2'-O-CEE protecting groups enables a reliable and complete two step deprotection, first with NH3aq-EtOH, then with TBAF in THF, without cleavage of internucleotidic linkages.
Umemoto
Tadashi
T
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha Bioscience bldg 702, Kashiwa, Chiba 277-8562, Japan.
Wada
Takeshi
T
D017665:Hydroxyl Radical / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D009570:Nitriles; D009843:Oligoribonucleotides; D014753:Vinyl Compounds; C521140:vinyloxypropionitrile; D017665:Hydroxyl Radical