title: Chromophoric 5'-O-Silyl protection of N-protected 2'-ACE ribonucleosides for solid-phase RNA synthesis.
abstract: Recent advances in the understanding of the pivotal roles played by endogenous small RNAs in gene regulation have resulted in a substantial and rapidly growing market for synthetic RNA. 5'-Silyl-2'-ACE chemistry has proven to be a robust and reliable technology for the synthesis of oligoribonucleotides. This unit describes an important improvement to this chemistry, by adding a cycle-to-cycle traceability analogous to that inherent in 5'-dimethoxytrityl-based approaches. This is achieved by first regioselectively introducing a 5'-alkynylsilyl protecting group onto the 2'-ACE-protected nucleosides. The 5'-alkynylsilyl group is then reacted with an azide derivative of the chromophore Disperse Red 1, which enables spectrophotometric interrogation of each coupling step following 5'-deprotection. Finally, the protected nucleosides are elaborated into their 3'-phosphoramidite derivatives for use in solid-phase RNA synthesis.
authors.affiliation: ThermoFisher Scientific, Dharmacon Products, Lafayette, Colorado, USA.
authors.forename: Michael O
authors.initials: MO
authors.lastname: Delaney
authors.forename: Angela
authors.initials: A
authors.lastname: Thomas
authors.forename: Chris
authors.initials: C
authors.lastname: Ricketts
authors.forename: David E
authors.initials: DE
authors.lastname: Kitchen
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Kaiser
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D012313:RNA / Q000138:chemical synthesis*; D012263:Ribonucleosides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: D012263:Ribonucleosides; D012313:RNA