title: Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis.
abstract: Access to 3-deazaadenosine (c3A) building blocks for RNA solid-phase synthesis represents a severe bottleneck in modern RNA research, in particular for atomic mutagenesis experiments to explore mechanistic aspects of ribozyme catalysis. Here, we report the 5-step synthesis of a c3A phosphoramidite from cost-affordable starting materials. The key reaction is a silyl-Hilbert-Johnson nucleosidation using unprotected 6-amino-3-deazapurine and benzoyl-protected 1-O-acetylribose. The novel path is superior to previously described syntheses in terms of efficacy and ease of laboratory handling.
authors.affiliation: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Austria.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Mairhofer
authors.affiliation: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Austria.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Fuchs
authors.affiliation: Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Austria.
authors.forename: Ronald
authors.initials: R
authors.lastname: Micura
keywords: deazapurine nucleoside; nucleosidation; protection groups; ribozymes