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Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties.

Abstract：

:Previously, we reported 2-N-carbamoylguanine (cmG) as a guanine analog. We further studied the synthetic protocol and hybridization properties of oligodeoxynucleotides (ODNs) incorporating cmG. These ODNs were synthesized using the phosphoramidite of cmG without protection of the 6-O position. However, the isolated products were contaminated with deacylated products having guanine in place of cmG. The detailed analysis of the synthetic process suggested that the deacylation resulted from the reaction of the carbamoyl moiety with capping reagents. Protection of the 6-O position suppressed the side reaction. The thermal stability of the DNA duplexes incorporating cmG was analyzed. An analysis of T(m) values revealed that the base discrimination ability of cmG was comparable to or higher than that of the canonical guanine depending on the flanking bases.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Sasami T,Odawara Y,Ohkubo A,Sekine M,Seio K

doi

10.1016/j.bmc.2008.11.042

subject

Has Abstract

pub_date

2009-02-01 00:00:00

pages

1398-403

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)01124-3

journal_volume

17

pub_type

杂志文章

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