Solid-phase synthesis of oligodeoxynucleotides using nucleobase N -unprotected oxazaphospholidine derivatives bearing a long alkyl chain

In this study, we developed a new approach for the solid-phase synthesis of oligodeoxynucleotides (ODNs) using nucleobase-unprotected oxazaphospholidine derivatives. We tackled the problem of the difficult purification of N -unprotected monomers due to their high affinity to silica gel by introducin...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-09, Vol.21 (37), p.7580-7592
Main Authors: Kakuta, Kiyoshi, Kasahara, Ryouta, Sato, Kazuki, Wada, Takeshi
Format: Article
Language:English
Subjects:
Functional groups
Monomers
Oligonucleotides
Silica
Silica gel
Solid phase methods
Solid phase synthesis
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Summary:In this study, we developed a new approach for the solid-phase synthesis of oligodeoxynucleotides (ODNs) using nucleobase-unprotected oxazaphospholidine derivatives. We tackled the problem of the difficult purification of N -unprotected monomers due to their high affinity to silica gel by introducing a tetrahydrogeranyl group into the oxazaphospholidine monomers, thereby enhancing the lipophilicity and facilitating the isolation. In addition, the cyclic structure of oxazaphospholidine enabled a hydroxy-group-selective condensation with sufficient efficiency. Unmodified and boranophosphate/phosphate chimeric ODNs were successfully synthesized using this strategy. This synthetic method can be expected to afford ODNs containing base-labile functional groups.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01255g