Synthesis of 3′-fluoro-4′-amino-hexitol nucleosides with a pyrimidine nucleobase as building blocks for oligonucleotides

Jabgunde, Amit M.; Patil, Rahul S.; De, Swarup; Lescrinier, Eveline; Jonghe, Steven De; Beigelman, Leonid; Herdewijn, Piet

doi:10.1016/j.tet.2019.01.026

Cited by 2 publications

(3 citation statements)

References 21 publications

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“…Herdewijn recently published the synthesis of 4'-aminotritylhexitol nucleosides for the eventual synthesis of N4' → P6' phosphoramidates of aminohexitol nucleic acids (AHNA) [ 229 ], as well as the synthesis of 3'-fluoro-4'-aminohexitol nucleosides which contain both the 3'-fluoro functionality and the N4' → P6' phosphoramidate linkage [ 230 ].…”

Section: Reviewmentioning

confidence: 99%

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

Liczner¹,

Duke²,

Juneau³

et al. 2021

Beilstein J. Org. Chem.

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Over the past 25 years, the acceleration of achievements in the development of oligonucleotide-based therapeutics has resulted in numerous new drugs making it to the market for the treatment of various diseases. Oligonucleotides with alterations to their scaffold, prepared with modified nucleosides and solid-phase synthesis, have yielded molecules with interesting biophysical properties that bind to their targets and are tolerated by the cellular machinery to elicit a therapeutic outcome. Structural techniques, such as crystallography, have provided insights to rationalize numerous properties including binding affinity, nuclease stability, and trends observed in the gene silencing. In this review, we discuss the chemistry, biophysical, and structural properties of a number of chemically modified oligonucleotides that have been explored for gene silencing.

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Section: Reviewmentioning

confidence: 99%

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

Liczner¹,

Duke²,

Juneau³

et al. 2021

Beilstein J. Org. Chem.

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“…The protected hexitol nucleosides are important buildingblocks for the synthesis of a new class of oligonucleotides which can be prominent congeners of hexitol nucleic acids, mannitol nucleic acids, 3'-methoxy-altritol nucleic acids and altritol nucleic acids. [102] Herdewijn and his co-workers [103] reported the synthesis of the protected…”

Section: Miscellaneousmentioning

confidence: 99%

“…The protected hexitol nucleosides are important building‐blocks for the synthesis of a new class of oligonucleotides which can be prominent congeners of hexitol nucleic acids, mannitol nucleic acids, 3′‐methoxy‐altritol nucleic acids and altritol nucleic acids [102] . Herdewijn and his co‐workers [103] reported the synthesis of the protected 3′‐fluoro‐4′‐amino‐hexitol nucleosides containing uracil and cytosine nucleobase from commercially available 1,5 : 2,3‐dianhydro‐4,6‐benzylidene‐allitol 30 in 15 steps via mannitol intermediate. The introduction of the azido functionality to afford 4′‐azido nucleoside 30 a in moderate yield (48 %) occurred via opening of an anhydro‐nucleoside with the retention of configuration.…”

Section: Nucleosidesmentioning

confidence: 99%

Strategies for the Synthesis of Fluorinated Nucleosides, Nucleotides and Oligonucleotides

Shet

Sahu

Sanghvi³

et al. 2022

The Chemical Record

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Fluorinated nucleosides and oligonucleotides are of specific interest as probes for studying nucleic acids interaction, structures, biological transformations, and its biomedical applications. Among various modifications of oligonucleotides, fluorination of preformed nucleoside and/or nucleotides have recently gained attention owing to the unique properties of fluorine atoms imparting medicinal properties with respect to the small size, electronegativity, lipophilicity, and ability for stereochemical control. This review deals with synthetic protocols for selective fluorination either at sugar or base moiety in a preformed nucleosides, nucleotides and nucleic acids using specific fluorinating reagents.

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Synthesis of 3′-fluoro-4′-amino-hexitol nucleosides with a pyrimidine nucleobase as building blocks for oligonucleotides

Cited by 2 publications

References 21 publications

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

Strategies for the Synthesis of Fluorinated Nucleosides, Nucleotides and Oligonucleotides

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