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. 1986 Mar 11;14(5):2171–2185. doi: 10.1093/nar/14.5.2171

Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.

J E Marugg, E de Vroom, C E Dreef, M Tromp, G A van der Marel, J H van Boom
PMCID: PMC339650  PMID: 3457366

Abstract

Dinucleoside methylphosphonates can easily be prepared starting from properly protected d-nucleosides and the bifunctional phosphorylating reagent methyl-O,O-bis(1-benzotriazolyl)phosphate. Separation of the diastereoisomers of 5'-DMTR-d-Ap(Me)T-3'-lev affords optically pure dinucleoside methylphosphonates which, after removal of the 3'-levulinoyl group, have been used for the synthesis of the two optically pure diastereoisomers of the hexamer d-CpGpAp(Me)TpCpG. Further, a one-pot procedure for the preparation of uridine-3',5'-cyclic methylphosphonate will be described. We also found that 3',5'-methylphosphonate linkages in RNA are not stable towards mild acid treatment.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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