On the Synthesis of Oligonucleotides Interconnected through Pyrophosphate Linkages

European Journal of Organic Chemistry

Volumn 2015, Issue 27, 2015, Pages 6084-6091

  Kistemaker, Hans A V ^a   Meeuwenoord, Nico J ^a   Overkleeft, Herman S ^a   Van Der Marel, Gijsbert A ^a   Filippov, Dmitri V ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Oligonucleotides; Phosphorylation; Pyrophosphate; Solid phase synthesis

Indexed keywords

EID: 84941600782     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201500911     Document Type: Article

References (30)

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29. The solubility of phosphates and pyrophosphates in DMSO is poor, as was observed for our compounds 26-29, making DMSO an inappropriate solvent for NMR analysis of these compounds. The stability of pyrophosphate(s) under acidic conditions is questionable, it is therefore a common practice to isolate and store these as salts of alkali metals, ammonia or tertiary amines. We followed in our study the conventional practice and handled the isolated pyrophosphate oligonucleotides as ammonium salts, except in the cases when we tried to make direct spectroscopic comparison of our products with those reported by Parang.
30. Decomposition has probably taken place in course of lyophilization of acidified pyrophosphate oligonucleotide 28 because we have started with purified homogeneous material in the ammonium form. When 28 was dissolved in D2O, treated with strong cation exchange resin to transform 28 to the acidic (protonated) form and subjected to 31P- and 1H-NMR spectroscopy, without prior lyophylization, the resulting spectra (see Supporting Information) proved to be only slightly different from those of 28 in the ammonium form (see Supporting Information). The 31P-NMR spectrum of 28 in acid form is clearly distinct from the one reported by Parang for the same oligonucleotide. Lyophilization of this protonated compound 28, however, shows decomposition of the material as was observed by 1H- and 31P-NMR spectroscopy (see Supporting Information).