title: Oligonucleotide duplexes containing 2'-amino-2'-deoxycytidines: thermal stability and chemical reactivity.
abstract: 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.
authors.affiliation: Max-Planck-Institut für Experimentelle Medizin, Göttingen, Germany.
authors.forename: H
authors.initials: H
authors.lastname: Aurup
authors.forename: T
authors.initials: T
authors.lastname: Tuschl
authors.forename: F
authors.initials: F
authors.lastname: Benseler
authors.forename: J
authors.initials: J
authors.lastname: Ludwig
authors.forename: F
authors.initials: F
authors.lastname: Eckstein
mesh_terms: 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
chemical_list: D000588:Amines; D003845:Deoxycytosine Nucleotides; D009838:Oligodeoxyribonucleotides; D003841:Deoxycytidine