Diastereomer separation of azobenzene-tethered oligodeoxyribonucleotides and determination of their absolute configurations by enzymatic digestion.
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.
Liang
Xingguo
X
Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Nagoya, Japan.
Komiyama
Makoto
M
Asanuma
Hiroyuki
H
D001391:Azo Compounds / Q000737:chemistry* / Q000378:metabolism; D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D007364:Intercalating Agents / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000235:genetics / Q000302:isolation & purification* / Q000378:metabolism; D043264:Phosphodiesterase I / Q000378:metabolism*; D013237:Stereoisomerism
D001391:Azo Compounds; D007364:Intercalating Agents; D009838:Oligodeoxyribonucleotides; D043264:Phosphodiesterase I; C009850:azobenzene