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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.

Original publication

DOI

10.1039/c6cc08473g

Type

Journal article

Journal

Chem Commun (Camb)

Publication Date

03/01/2017

Volume

53

Pages

541 - 544

Keywords

Animals, Apolipoproteins B, Base Sequence, COS Cells, Chlorocebus aethiops, Ferrochelatase, Humans, Oligonucleotides, Antisense, Phosphorothioate Oligonucleotides, RNA, Messenger, Stereoisomerism