ArticleOrganic letters2017
Concurrent Hydrogenation of Three Functional Groups Enables Synthesis of C3'-Homologated Nucleoside Amino Acids.
Article in Organic letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 13 citations in OpenAlex.
- Amide Internucleoside Linkages Suppress the MicroRNA-like Off-Target Activity of Short Interfering RNA.ACS chemical biology · 2025Article
- An LNA-amide modification that enhances the cell uptake and activity of phosphorothioate exon-skipping oligonucleotides.Nature communications · 2022Article
- Optimization of Automated Synthesis of Amide-Linked RNA.ACS omega · 2022Article
- Amide-Modified RNA: Using Protein Backbone to Modulate Function of Short Interfering RNAs.Accounts of chemical research · 2020Article
- Synthesis and Biological Activity of Short Interfering RNAs Having Several Consecutive Amide Internucleoside Linkages.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Design, Synthesis and Molecular Modeling Study of Conjugates of ADP and Morpholino Nucleosides as A Novel Class of Inhibitors of PARP-1, PARP-2 and PARP-3.International journal of molecular sciences · 2019Article
- A hydroxamic-acid-containing nucleoside inhibits DNA repair nuclease SNM1A.Organic & biomolecular chemistry · 2019Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Internucleoside amide linkages are excellent mimics of phosphodiesters in RNA and may be used to optimize the properties of short interfering RNAs. Herein we report a remarkably straightforward, efficient and step economic synthesis of C3'-homologated uridine and adenosine amino acids starting from nucleosides in six steps (31% overall yield) and eight steps (16% overall yield), respectively. The key enabling step is a one-pot multifunctional group transformation including a stereoselective hydrogenation, termed "Global Hydrogenation".
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Registered trials
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