2-Amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-Oligodeoxynucleotides with RNA target

Magali Naval; Thibaut Michel; Jean-Jacques Vasseur; Francoise Debart

doi:10.1016/s0960-894x(02)00215-9

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2-Amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-Oligodeoxynucleotides with RNA target

Journal article

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Peer reviewed

2-Amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-Oligodeoxynucleotides with RNA target

Magali Naval, Thibaut Michel, Jean-Jacques Vasseur and Francoise Debart

Bioorganic and Medicinal Chemistry Letters, Vol.12(11), pp.1435-1438

2002

DOI: https://doi.org/10.1016/s0960-894x(02)00215-9

PMID: 12031314

Abstract

Amides

Base Sequence

Oligodeoxyribonucleotides

Phosphoric Acids

RNA

Cytosine

DNA, Complementary

Deoxyadenosines

Guanosine

Hot Temperature

Nucleic Acid Denaturation

Nucleic Acid Heteroduplexes

Nucleic Acid Hybridization

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.

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Title: 2-Amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-Oligodeoxynucleotides with RNA target
Creators - without role: Magali Naval - Université de Montpellier
Thibaut Michel - Chimie organique biomoléculaire de synthèse
Jean-Jacques Vasseur - Chimie organique biomoléculaire de synthèse
Francoise Debart - Chimie organique biomoléculaire de synthèse
Publication Details: Bioorganic and Medicinal Chemistry Letters, Vol.12(11), pp.1435-1438
Grant note: This work was supported bygrants from the Association pour la Recherche contre le Cancer (ARC, France). N.M. thanks the ARC for the award of a research studentship
Identifiers: 9946654709311
Academic Unit: Université de Montpellier
Language: English
Resource Type: Journal article
Local Fields: hal-04600717