Refereed journal article or data article (A1)

N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) - a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties




List of AuthorsAfari Mark N. K., Virta Pasi, Lönnberg Tuomas

PublisherROYAL SOC CHEMISTRY

Publication year2022

JournalOrganic and Biomolecular Chemistry

Journal name in sourceORGANIC & BIOMOLECULAR CHEMISTRY

Journal acronymORG BIOMOL CHEM

Volume number20

Issue number17

Start page3480

End page3485

Number of pages6

ISSN1477-0520

eISSN1477-0539

DOIhttp://dx.doi.org/10.1039/d2ob00465h

URLhttps://pubs.rsc.org/en/content/articlelanding/2022/OB/D2OB00465H

Self-archived copy’s web addresshttps://research.utu.fi/converis/portal/detail/Publication/175160408


Abstract
(2R,3S)-4-(Methoxyamino)butane-1,2,3-triol was converted into a protected phosphoramidite building block and incorporated into the middle of a short DNA oligonucleotide. O1 and O3 of the (2R,3S)-4-(methoxyamino)butane-1,2,3-triol were engaged in phosphodiester linkages, leaving O2 and the methoxyamino function available to form an N-methoxy-1,3-oxazinane ring through reaction with an aldehyde. In modified oligonucleotides thus obtained, the oxazinane ring formally replaces the furanose ring and the aldehyde, the base moiety of natural nucleosides. The feasibility of synthesizing base-modified oligonucleotides by this approach was demonstrated with several aromatic and aliphatic aldehydes featuring various functional groups.

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Last updated on 2023-02-06 at 10:03