312738-47-9Relevant academic research and scientific papers
2′-Deoxyuridine and 2′-deoxyisocytidine as constituents of DNA with parallel chain orientation: The stabilization of the iCd·Gd base pair by the 5-methyl group
Seela, Frank,He, Yang
, p. 2527 - 2540 (2007/10/03)
Parallel-stranded oligonucleotides containing 2′-deoxyuridine (2) and 2′-deoxyisocytidine (4) were synthesized. The phosphoramidite 11 employed in the solid-phase synthesis carries a (dimethylamino)methylidene residue as amino-protecting group. This group stabilizes the acid-labile glycosylic bond of 4 and enables the base-catalyzed deprotection of oligonucleotides without degrading the nucleoside 4 residues. Oligonucleotide duplexes incorporating the 5-Me derivatives of 2 (→2′-deoxythymidine) and 4 (→2′-deoxy-5-methylisocytidine), which are more stable than those containing the unmethylated nucleosides, were also compared. Depending on the nearest-neighbor environment. Me groups provide an additional stabilization through Me/Me contacts or Me/backbone interactions.
