Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemical synthesis
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Amides / chemistry
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Base Sequence
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Cytosine / chemistry
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DNA, Complementary / chemistry
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Deoxyadenosines / chemical synthesis
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Deoxyadenosines / chemistry*
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Guanosine / analogs & derivatives
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Guanosine / chemistry
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Hot Temperature
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Nucleic Acid Denaturation
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Nucleic Acid Heteroduplexes / chemistry
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Nucleic Acid Hybridization
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Oligodeoxyribonucleotides / chemical synthesis*
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Oligodeoxyribonucleotides / chemistry
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Phosphoric Acids / chemical synthesis
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Phosphoric Acids / chemistry
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RNA / chemistry*
Substances
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Amides
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DNA, Complementary
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Deoxyadenosines
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Nucleic Acid Heteroduplexes
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Oligodeoxyribonucleotides
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Phosphoric Acids
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2'-amino-2'-deoxyadenosine
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Guanosine
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RNA
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Cytosine
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phosphoramidic acid