ArticleScience (New York, N.Y.)2021
Catalytic asymmetric and stereodivergent oligonucleotide synthesis.
Article in Science (New York, N.Y.), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Article
- Carbene-catalyzed site-selective sulfonylation and modular edition of monosaccharides for hydroxyl group stereoinversion and swapping.Nature communications · 2026Article
- Stereocontrolled Synthesis of Dimethylamino Phosphorochloridate Monomers toward Stereopure Phosphorodiamidate Morpholino Oligonucleotides.The Journal of organic chemistry · 2026Article
- Stepwise-controllable catalytic asymmetric Atherton-Todd reaction to access diverse P(V)-stereogenic compounds.Nature chemistry · 2026Article
- Article
- RNA chemistry and therapeutics.Nature reviews. Drug discovery · 2025Review
- Pathway to P(V)-Stereogenic Phosphoramidates by Enantioselective Yttrium Catalysis.Journal of the American Chemical Society · 2025Article
- Couple-close construction of non-classical boron cluster-phosphonium conjugates.Nature communications · 2024Article
- A highly efficient catalytic method for the synthesis of phosphite diesters.Chemical science · 2024Article
- Orthogonal Hydroxyl Functionalization of cGAMP Confers Metabolic Stability and Enables Antibody Conjugation.ACS central science · 2023Article
- Catalyst control over pentavalent stereocentres.Nature communications · 2023Article
- Article
- Cap analogs with a hydrophobic photocleavable tag enable facile purification of fully capped mRNA with various cap structures.Nature communications · 2023Article
- 10th anniversary of discovering cGAMP: synthesis and beyond.Organic chemistry frontiers : an international journal of organic chemistry · 2023Article
- Advances in the Synthesis and Analysis of Biologically Active Phosphometabolites.International journal of molecular sciences · 2023Review
- Metal-FreeOrganic letters · 2023Article
- Biocatalytic Synthesis of Antiviral Nucleosides, Cyclic Dinucleotides, and Oligonucleotide Therapies.JACS Au · 2023Review
- Stereospecific nickel-catalyzed [4+2] heteroannulation of alkynes with aminophosphanes.Science advances · 2023Article
- Organocatalytic asymmetric synthesis of P-stereogenic molecules.Frontiers in chemistry · 2023Review
- Improvements to Hybridization-Ligation ELISA Methods to Overcome Bioanalytical Challenges Posed by Novel Oligonucleotide Therapeutics.Nucleic acid therapeutics · 2022Article
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Authors and funding
6 authors.
Funding
Abstract
We report the catalytic stereocontrolled synthesis of dinucleotides. We have demonstrated, for the first time to our knowledge, that chiral phosphoric acid (CPA) catalysts control the formation of stereogenic phosphorous centers during phosphoramidite transfer. Unprecedented levels of diastereodivergence have also been demonstrated, enabling access to either phosphite diastereomer. Two different CPA scaffolds have proven to be essential for achieving stereodivergence: peptide-embedded phosphothreonine-derived CPAs, which reinforce and amplify the inherent substrate preference, and C2-symmetric BINOL-derived CPAs, which completely overturn this stereochemical preference. The presently reported catalytic method does not require stoichiometric activators or chiral auxiliaries and enables asymmetric catalysis with readily available phosphoramidites. The method was applied to the stereocontrolled synthesis of diastereomeric dinucleotides as well as cyclic dinucleotides, which are of broad interest in immuno-oncology as agonists of the stimulator of interferon genes (STING) pathway.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.