2 `-deoxyuridine and 2 `-deoxyisocytidine as constituents of DNA with parallel chain orientation: The stabilization of the iC(d)center dot Gd base pair by the 5-methyl group

Autor(en): Seela, F
He, Y
Stichwörter: 2'-DEOXYISOGUANOSINE; CENTER-DOT-DU; Chemistry; Chemistry, Multidisciplinary; CYTOSINE; ENZYMATIC INCORPORATION; ISOGUANINE; METHYLATION; OLIGONUCLEOTIDE DUPLEXES; RNA; STABILITY; STRANDED DUPLEX DNA
Erscheinungsdatum: 2000
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 83
Ausgabe: 9
Startseite: 2527
Seitenende: 2540
Zusammenfassung: 
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-5methylisocytidine), 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.
ISSN: 0018019X
DOI: 10.1002/1522-2675(20000906)83:9<2527::AID-HLCA2527>3.0.CO;2-D

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