A1 Refereed original research article in a scientific journal
N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) - a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties
Authors: Afari Mark N. K., Virta Pasi, Lönnberg Tuomas
Publisher: ROYAL SOC CHEMISTRY
Publication year: 2022
Journal: Organic and Biomolecular Chemistry
Journal name in source: ORGANIC & BIOMOLECULAR CHEMISTRY
Journal acronym: ORG BIOMOL CHEM
Volume: 20
Issue: 17
First page : 3480
Last page: 3485
Number of pages: 6
ISSN: 1477-0520
eISSN: 1477-0539
DOI: https://doi.org/10.1039/d2ob00465h
Web address : https://pubs.rsc.org/en/content/articlelanding/2022/OB/D2OB00465H
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/175160408
(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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