A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) - a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties
Tekijät: Afari Mark N. K., Virta Pasi, Lönnberg Tuomas
Kustantaja: ROYAL SOC CHEMISTRY
Julkaisuvuosi: 2022
Journal: Organic and Biomolecular Chemistry
Tietokannassa oleva lehden nimi: ORGANIC & BIOMOLECULAR CHEMISTRY
Lehden akronyymi: ORG BIOMOL CHEM
Vuosikerta: 20
Numero: 17
Aloitussivu: 3480
Lopetussivu: 3485
Sivujen määrä: 6
ISSN: 1477-0520
eISSN: 1477-0539
DOI: https://doi.org/10.1039/d2ob00465h
Verkko-osoite: https://pubs.rsc.org/en/content/articlelanding/2022/OB/D2OB00465H
Rinnakkaistallenteen osoite: 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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