Chemical synthesis of oligoribonucleotides with 2'-O-(2-cyanoethoxymethyl)-protected phosphoramidites.
An RNA synthetic method with 2-cyanoethoxymethyl (CEM) as the 2'-hydroxyl protecting group allows the synthesis of long oligoribonucleotides from CEM-amidites with an efficiency and final purity comparable to that obtained in DNA synthesis. The CEM-amidites give a high coupling efficiency, because the CEM group minimizes steric hindrance in the coupling reaction. The CEM group shows satisfactory stability under solid-phase synthetic conditions, avoids the generation of asymmetric centers, and is easily cleaved to give the final product. This unit describes the synthesis of the four CEM-amidites, the preparation of reagents, the solid-phase synthesis of oligoribonucleotides on an automated DNA synthesizer, and their deprotection.
Ohgi
Tadaaki
T
Discovery Research Laboratories, Nippon Shinyaku Co., Ltd., Ibaraki, Japan.
Kitagawa
Hidetoshi
H
Yano
Junichi
J
D002625:Chemistry, Organic / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D009843:Oligoribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite