2-(4-Tolylsulfonyl)ethoxymethyl (TEM)—a new 2′-OH protecting group for solid-supported RNA synthesis
Zhou, Chuanzheng; Honcharenko, Dmytro; Chattopadhyaya, Jyoti; Zhou Chuanzheng; Department of Bioorganic Chemistry, Box 581, Biomedical Center, Uppsala University; Honcharenko Dmytro; Department of Bioorganic Chemistry, Box 581, Biomedical Center, Uppsala University; Chattopadhyaya Jyoti; Department of Bioorganic Chemistry, Box 581, Biomedical Center, Uppsala University
Журнал:
Organic & Biomolecular Chemistry
Дата:
2007
Аннотация:
The 2-(4-tolylsulfonyl)ethoxymethyl (TEM) as a new 2â ²-OH protecting group is reported for solid-supported RNA synthesis using phosphoramidite chemistry. The usefulness of the 2â ²-O-TEM group is exemplified by the synthesis of 12 different oligo-RNAs of various sizes (14â 38 nucleotides long). The stepwise coupling yield varied from 97â 99% with an optimized coupling time of 120 s. The synthesis of all four pure phosphoramidite building blocks is also described. Two new reliable parameters, δC2â ² â δC3â ² and δH2â ² â δH3â ², have been suggested for the characterization of isomeric 2â ²-O-TEM and 3â ²-O-TEM as well as other isomeric mono 2â ²/3â ²-protected ribonucleoside derivatives. The most striking feature of this strategy is that the crude RNA prepared using our 2â ²-O-TEM strategy is sufficiently pure (>90%) for molecular biology research without any additional purification step, thereby making oligo-RNAs easily available at a relatively low cost, saving both time and lab resources.
297.0Кб