Tetrahedron p. 9481 - 9500 (1999)
Update date:2022-08-03
Topics:
Seela, Frank
He, Yang
Wei, Changfu
Parallel-stranded oligonucleotides containing 5-methylisocytosine- guanine and/or isoguanine-cytosine base pairs were prepared. The coupling efficiency was higher than 99% when the phosphoramidites of 2'-deoxy-5- methylisocytidine (2a) and of 2'-deoxyisoguanosine (3) were employed in solid-phase synthesis. The glycosylic bond of 2'-deoxy-5-methylisocytidine (1a) is stabilized against acid in the case of the amidine derivatives 4a, b. Depyrimidination occurs upon extended exposure to ammonia. The orientation of the parallel-stranded (ps) duplexes was unambiguously determined using the pyrene excimer fluorescence. The antiparallel (aps) duplex d(A12)·d(T12) (25.26) turned into the parallel orientation when two central adenine- thymine base pairs were replaced by isoguanine-cytosine pairs. The thermal stability of ps-duplexes containing 5-methylisocytosine-guanine base pairs was found to be significantly lower than that of duplexes with isoguanine, cytosine pairs. According to the CD spectra, ps-DNA-DNA or DNA-RNA hybrids show differences in their secondary structures compared to their aps counterparts.
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Doi:10.1007/BF02329590
(1998)Doi:10.1016/S0022-328X(99)00147-3
(1999)Doi:10.1021/jo0158985
(2001)Doi:10.1021/ol990137y
(1999)Doi:10.1016/S0040-4039(99)00972-7
(1999)Doi:10.1021/jo990245y
(1999)