Synthesis and cellular activity of stereochemically-pure 2’-O-(2-methoxyethyl)-phosphorothioate oligonucleotides

Li, Meiling; Lightfoot, Helen Louise; Halloy, Francois; Malinowska, Anna; Berk, Christian; Behera, Alok; Schümperli, Daniel; Hall, Jonathan (2017). Synthesis and cellular activity of stereochemically-pure 2’-O-(2-methoxyethyl)-phosphorothioate oligonucleotides. Chemical communications, 53(3), pp. 541-544. Royal Society of Chemistry 10.1039/C6CC08473G

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Stereochemically-pure 2’-O-(2-methoxyethyl)-phosphorothioate (PS-MOE) oligonucleotides were synthesized from new chiral oxazaphospholidine-containing nucleosides. Thermal stability studies showed that the incorporation of Rp-PS linkages increased RNA-binding affinity. In cells, a full Rp-PS-MOE splice-switching oligonucleotide targeting part of the ferrochelatase gene was more potent than its Sp-PS counterpart, but of similar potency to the stereorandom PS-parent sequence.

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