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. 2017 Dec 1;82(23):12003-12013.
doi: 10.1021/acs.joc.7b01484. Epub 2017 Oct 31.

Synthesis of 5'-Thio-3'-O-ribonucleoside Phosphoramidites

Nan-Sheng Li  1 , Jun Lu  1 , Joseph A Piccirilli  1
Affiliations

Synthesis of 5'-Thio-3'-O-ribonucleoside Phosphoramidites

Nan-Sheng Li et al. J Org Chem. .

Abstract

The chemical synthesis of phosphoramidite derivatives of all four 5'-deoxy-5'-thioribonucleosides is described. These phosphoramidites contained trityl (A, G, C, and U), dimethoxytrityl (A and G), or tert-butyldisulfanyl (G) as the 5'-S-protecting group. The application of several of these phosphoramidites for solid-phase synthesis of oligoribonucleotides containing a 2'-O-photocaged 5'-S-phosphorothiolate linkage or 5'-thiol-labeled RNAs is also further investigated.

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Figures

Figure 1.
Figure 1.
Structures of oligonucleotides containing a site-specific 5´-S-phosphorothiolate linkage. I: ODN with a 5´-PS DNA dinucleotide (dB1)-ps-(dB2); II: ODN with 5´-PS RNA/DNA dinucleotide (rB1)-ps-(dB2); III: ORN with a 5´-PS RNA dinucleotide (rB1)-ps-(rB2).
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See this image and copyright information in PMC

References

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