N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) - a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties
Lönnberg Tuomas; Afari Mark N. K.; Virta Pasi
N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) - a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties
Lönnberg Tuomas
Afari Mark N. K.
Virta Pasi
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ROYAL SOC CHEMISTRY
Julkaisun pysyvä osoite on:
https://urn.fi/URN:NBN:fi-fe2022081154357
https://urn.fi/URN:NBN:fi-fe2022081154357
Tiivistelmä
(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.
Kokoelmat
- Rinnakkaistallenteet [19207]