195375-63-4Relevant articles and documents
Synthesis of all four nucleoside-based β-amino acids as protected precursors for the synthesis of polyamide-DNA with alternating α-amino acid and nucleoside-β-amino acids
Bagmare, Seema,Varada, Manojkumar,Banerjee, Anjan,Kumar, Vaijayanti A.
, p. 1210 - 1216 (2013/02/23)
A simple approach is described for the synthesis of all four orthogonally protected nucleoside-β-amino acids from commercially available starting materials. Synthesis of a model tetrameric DNA sequence in 5′-3'direction employing trityl strategy and glycine as α-amino acid alternating with nucleoside-β amino acids is described.
A new approach to oligonucleotide N3′ → P5′ phosphoramidate building blocks
Zielinska, Daria,Pongracz, Krisztina,Gryaznov, Sergei M.
, p. 4495 - 4499 (2007/10/03)
A new synthetic approach to 5′-phosphoramidites of 3′-aminonucleosides was developed. The methodology relies upon the use of 3′-amino-2′,3′-dideoxynucleosides as the key starting materials. The final products were obtained in high yields via 2-3-step processes using selective introduction of orthogonal protective groups to the 3′-aminonucleoside sugar and base moieties.
N3′→P5′ Oligodeoxyribonucleotide Phosphoramidates: A New Method of Synthesis Based on a Phosphoramidite Amine-Exchange Reaction
Nelson, Jeffrey S.,Fearon, Karen L.,Nguyen, Mark Q.,McCurdy, Sarah N.,Frediani, Jeff E.,Foy, Michael F.,Hirschbein, Bernard L.
, p. 7278 - 7287 (2007/10/03)
A new method for the synthesis of N3′→P5′ phosphoramidate oligodeoxynucleotides is demonstrated. Described herein is the synthesis of the monomers utilized in the phosphoramidite amine-exchange process and the experimental details pertaining to this new mode of chain assembly. The phosphoramidite amine-exchange method generates coupling yields in the 92-95% range per cycle and further enables the synthesis of chimeric phosphoramidate/phosphodiester or phosphoramidate/ phosphorothioate oligonucleotides with no instrument modifications.
