Oligonucleotide duplexes containing 2'-amino-2'-deoxycytidines: thermal stability and chemical reactivity.
Thermal stabilities of oligonucleotides containing 2'-amino-2'-deoxycytidines were determined and compared to those of the unmodified oligonucleotides. The presence of the 2'-aminonucleoside destabilized duplexes in a RNA as well as a DNA context at pH 7 as well as at pH 5. The pKa of the 2'-amino group was determined by 13C-NMR spectroscopy to be 6.2. The reactivity of an oligonucleotide containing a 2'-aminonucleoside was exploited for the incorporation of rhodamine by its isothiocyanate derivative.
Aurup
H
H
Max-Planck-Institut für Experimentelle Medizin, Göttingen, Germany.
Tuschl
T
T
Benseler
F
F
Ludwig
J
J
Eckstein
F
F
D000588:Amines; D001483:Base Sequence; D003841:Deoxycytidine / Q000031:analogs & derivatives*; D003845:Deoxycytosine Nucleotides / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009691:Nucleic Acid Denaturation; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013696:Temperature; D013816:Thermodynamics
D000588:Amines; D003845:Deoxycytosine Nucleotides; D009838:Oligodeoxyribonucleotides; D003841:Deoxycytidine