title: An Unconventional Acid-Labile Nucleobase Protection Concept for Guanosine Phosphoramidites in RNA Solid-Phase Synthesis.
abstract: We present an innovative O6-tert-butyl/N2-tert-butyloxycarbonyl protection concept for guanosine (G) phosphoramidites. This concept is advantageous for 2'-modified G building blocks because of very efficient synthetic access when compared with existing routes that usually employ O6-(4-nitrophenyl)ethyl/N2-acyl protection or that start from 2-aminoadenosine involving enzymatic transformation into guanosine later on in the synthetic path. The new phosphoramidites are fully compatible with 2'-O-tBDMS or TOM phosphoramidites in standard RNA solid-phase synthesis and deprotection, and provide excellent quality of tailored RNAs for the growing range of applications in RNA biophysics, biochemistry, and biology.
authors.affiliation: Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020, Innsbruck, Austria.
authors.forename: Lukas
authors.initials: L
authors.lastname: Jud
authors.affiliation: Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020, Innsbruck, Austria.
authors.forename: Ronald
authors.identifier: http://orcid.org/0000-0003-2661-6105
authors.initials: R
authors.lastname: Micura
mesh_terms: D000143:Acids / Q000737:chemistry; D000241:Adenosine / Q000031:analogs & derivatives / Q000737:chemistry; D001483:Base Sequence; D006151:Guanosine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D009596:Nitrophenols / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012313:RNA / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000143:Acids; D009596:Nitrophenols; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D006151:Guanosine; C033854:2-aminoadenosine; C024719:4-nitrophenyl; D012313:RNA; D000241:Adenosine
keywords: RNA; nucleosides; oligonucleotides; protecting groups; solid-phase synthesis