2-Amino-alpha-2'-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate alpha-oligodeoxynucleotides with RNA target.
A new efficient synthesis of 2-amino-alpha-2'-deoxyadenosine and its incorporation into methoxyethylphosphoramidate alpha-oligodeoxynucleotides (ODNs) via H-phosphonate chemistry were reported. Thermal denaturation experiments demonstrated a significant stabilization of the complexes formed between these analogues and their RNA target (+2 degrees C/NH2A) relative to adenosine-containing phosphoramidate alpha-oligonucleotides. Concerning the binding specificity of these modified ODNs, unlike natural ODNs, discrimination against G pairing is higher and against C pairing is lower.
Naval
Magali
M
Laboratoire de Chimie Organique Biomoléculaire de Synthèse, UMR 5625 CNRS-UM II, CC 008, Université Montpellier II, Place Eugène Bataillon, 34095 Cedex 05, France.
Michel
Thibaut
T
Vasseur
Jean-Jacques
JJ
Debart
Françoise
F
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D001483:Base Sequence; D003596:Cytosine / Q000737:chemistry; D018076:DNA, Complementary / Q000737:chemistry; D003839:Deoxyadenosines / Q000138:chemical synthesis / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives / Q000737:chemistry; D006358:Hot Temperature; D009691:Nucleic Acid Denaturation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids / Q000138:chemical synthesis / Q000737:chemistry; D012313:RNA / Q000737:chemistry*
D000577:Amides; D018076:DNA, Complementary; D003839:Deoxyadenosines; D009692:Nucleic Acid Heteroduplexes; D009838:Oligodeoxyribonucleotides; D010756:Phosphoric Acids; C003965:2'-amino-2'-deoxyadenosine; D006151:Guanosine; D012313:RNA; D003596:Cytosine; C011067:phosphoramidic acid