title: 2-(4-Tolylsulfonyl)ethoxymethyl (TEM)-a new 2'-OH protecting group for solid-supported RNA synthesis.
abstract: The 2-(4-tolylsulfonyl)ethoxymethyl (TEM) as a new 2'-OH protecting group is reported for solid-supported RNA synthesis using phosphoramidite chemistry. The usefulness of the 2'-O-TEM group is exemplified by the synthesis of 12 different oligo-RNAs of various sizes (14-38 nucleotides long). The stepwise coupling yield varied from 97-99% with an optimized coupling time of 120 s. The synthesis of all four pure phosphoramidite building blocks is also described. Two new reliable parameters, delta(C2')-delta(C3') and delta(H2')-delta(H3'), have been suggested for the characterization of isomeric 2'-O-TEM and 3'-O-TEM as well as other isomeric mono 2'/3'-protected ribonucleoside derivatives. The most striking feature of this strategy is that the crude RNA prepared using our 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.
authors.affiliation: Department of Bioorganic Chemistry, Box 581, Biomedical Center, Uppsala University, S-751 23, Uppsala, Sweden.
authors.forename: Chuanzheng
authors.initials: C
authors.lastname: Zhou
authors.forename: Dmytro
authors.initials: D
authors.lastname: Honcharenko
authors.forename: Jyoti
authors.initials: J
authors.lastname: Chattopadhyaya
mesh_terms: D001483:Base Sequence; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D018736:DNA Adducts; D004583:Electrons; D006878:Hydroxides; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008969:Molecular Sequence Data; D009841:Oligonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D012313:RNA / Q000737:chemistry*; D012263:Ribonucleosides / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*; D013997:Time Factors
chemical_list: D018736:DNA Adducts; D006878:Hydroxides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D012263:Ribonucleosides; D013450:Sulfones; C434331:phosphoramidite; D012313:RNA; C031356:hydroxide ion