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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.

SUBMITTER: Mairhofer E

PROVIDER: S-EPMC5238537 | biostudies-other | 2016

REPOSITORIES: biostudies-other

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Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis.

Mairhofer Elisabeth E Fuchs Elisabeth E Micura Ronald R

Beilstein journal of organic chemistry 20161128

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-acetyl ...[more]

PMID: 28144324

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