Chemical Synthesis of Oligonucleotides: From Dream to Automation

Pon, Richard T.

doi:10.1002/chin.200408304

Cited by 1 publication

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“…However, this is not the case for therapeutic antisense oligonucleotides, which are prepared routinely in multigram amounts. In that scale, their quantity is conveniently determined by weighting [ 7 , 8 ], and proper accuracy of measurements requires that the stoichiometric contents of the cation are maintained.…”

Section: Resultsmentioning

confidence: 99%

The case of triethylammonium cation loss during purification of certain nucleotide analogues: a cautionary note

et al. 2014

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Nucleotides, their analogues, and other phosphate esters and phosphoramidates often contain the triethylammonium cation as a counterion. We found that this may be lost during chromatographic purification or concentration of solutions, yielding products in acidic forms or containing sub-stoichiometric amounts of the counterion. This in turn may be detrimental, e.g., due to possible decomposition of a compound or inaccurate sample preparation. Correlations between the structure of studied compounds and their susceptibility for cation loss were analyzed. Modifications in preparative techniques were developed to obtain the studied compounds with stoichiometric anion to cation ratios.ᅟGraphical AbstractTriethylammonium salts of phosphate esters and phosphoramidates may lose the cationic component during chromatography or evaporation of solventElectronic supplementary materialThe online version of this article (doi:10.1007/s00216-014-8397-0) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%