Solid-phase synthesis of the self-complementary hexamer d(c7GpCpc7GpCpc7GpC) via the O-3′-phosphoramidite of 7-deaza-2′-deoxyguanosine
- 11 February 1985
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 13 (3), 911-926
- https://doi.org/10.1093/nar/13.3.911
Abstract
The synthesis of the 0–3′-phosphoramidite of a suitably protected 7-deaza-2′-deoxyguanosine (c 7 G) which is an isostere of 2′-deoxyguanosine is described. The phosphoramidite of the modified nucleoside was used in the synthesis of the self-complementary hexamer d(c 7 GpCpc 7 GpCpc 7 GpC) on function alized silica gel in a mini-reactor. As expected from the parent hexamer d(GpCpGpCpGpC) the isosteric d(c 7 GpCpc 7 GpCpc 7 GpC) exhibits a rigid secondary structure (22% hypochromicity at 280 nm) and forms a duplex in 1 M aqueous sodium chloride solution. Due to the altered π-electron system of the pyrrolo[2, 3-d]pyrimidine nucleobase, which affects base stacking and hydrogen bonding, the T m of the modified duplex is decreased by 10°C compared to that of the parent purine hexamer. Moreover, it is expected that the incor poration of c 7 G influences the pitch of the helix.Keywords
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