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. 1996 Nov 15;24(22):4584–4591. doi: 10.1093/nar/24.22.4584

Synthesis and thermodynamics of oligonucleotides containing chirally pure R(P) methylphosphonate linkages.

M A Reynolds 1, R I Hogrefe 1, J A Jaeger 1, D A Schwartz 1, T A Riley 1, W B Marvin 1, W J Daily 1, M M Vaghefi 1, T A Beck 1, S K Knowles 1, R E Klem 1, L J Arnold Jr 1
PMCID: PMC146287  PMID: 8948653

Abstract

Methylphosphonate (MP) oligodeoxynucleotides (MPOs) are metabolically stable analogs of conventional DNA containing a methyl group in place of one of the non-bonding phosphoryl oxygens. All 16 possible chiral R(P) MP dinucleotides were synthesized and derivatized for automated oligonucleotide synthesis. These dimer synthons can be used to prepare (i) all-MP linked oligonucleotides having defined R(P) chirality at every other position (R(P) chirally enriched MPOs) or (ii) alternating R(P) MP/phosphodiester backbone oligonucleotides, depending on the composition of the 3'-coupling group. Chirally pure dimer synthons were also prepared with 2'-O-methyl sugar modifications. Oligonucleotides prepared with these R(P) chiral methylphosphonate linkage synthons bind RNA with significantly higher affinity than racemic MPOs.

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Selected References

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