Diastereomer separation of azobenzene-tethered oligodeoxyribonucleotides and determination of their absolute configurations by enzymatic digestion

作者：Liang Xingguo; Komiyama Makoto; Asanuma Hiroyuki^*

来源：Nucleosides Nucleotides & Nucleic Acids, 2008, 27(4): 332-350.

DOI：10.1080/15257770801943917

• diastereomer separation
• modified oligodeoxynucleotide
• absolute configuration
• enzymatic digestion
• phosphodiesterase

Two diastereomers were produced by the introduction of azobenzene-tethering prochiral linker (2,2-bis(hydroxymethyl)propionic acid) in the modified ODN, which had been used for the photoregulation of DNA functions. We found that this modified ODN with sequence 5';-...pNpXpN...-3'; (p = phosphate; N = nucleoside; X = azobenzene residue) could be digested to pX (the phosphate at the 5'; side of X was left) by an over excess of Phosphodiesterase I. By comparing the retention time of pX from the separated diastereomer with that of authentic R- or S-pX on chiral HPLC, absolute configuration could be easily determined.

• 出版日期2008