2. Academic Validation
  3. Synthesis and cellular activity of stereochemically-pure 2'-O-(2-methoxyethyl)-phosphorothioate oligonucleotides

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

  • Chem Commun (Camb). 2017 Jan 3;53(3):541-544. doi: 10.1039/c6cc08473g.
M Li 1,  H L Lightfoot 1,  F Halloy 1,  A L Malinowska 1,  C Berk 1,  A Behera 1,  D Schümperli 2,  J Hall 1
Affiliations

Affiliations

  • 1 Institute of Pharmaceutical Sciences, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich, Switzerland. jonathan.hall@pharma.ethz.ch.
  • 2 Institute of Cell Biology, University of Bern, 3012 Bern, Switzerland.
PMID: 27966701 DOI: 10.1039/c6cc08473g
Abstract

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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