title: The case of triethylammonium cation loss during purification of certain nucleotide analogues: a cautionary note.
abstract: 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.
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704, Poznań, Poland.
authors.forename: Krystian
authors.initials: K
authors.lastname: Kolodziej
authors.forename: Joanna
authors.initials: J
authors.lastname: Romanowska
authors.forename: Jacek
authors.initials: J
authors.lastname: Stawinski
authors.forename: Adam
authors.initials: A
authors.lastname: Kraszewski
authors.forename: Michal
authors.initials: M
authors.lastname: Sobkowski
mesh_terms: D009711:Nucleotides / Q000032:analysis*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
chemical_list: D009711:Nucleotides; D000644:Quaternary Ammonium Compounds; C066585:triethylammonium cation