Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 12, Issue -, Pages 2556-2562Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.12.250
Keywords
deazapurine nucleoside; nucleosidation; protection groups; ribozymes
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Funding
- Austrian Science Fund FWF [I1040, P27947]
- Austrian Science Fund (FWF) [I1040, P27947] Funding Source: Austrian Science Fund (FWF)
- Austrian Science Fund (FWF) [I 1040, P 27947] Funding Source: researchfish
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Access to 3-deazaadenosine (c(3)A) 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 c(3)A 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.
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