Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues

被引：90

作者：

Haraguchi, K ^{[1
]}

Delaney, MO ^{[1
]}

Wiederholt, CJ ^{[1
]}

Sambandam, A ^{[1
]}

Hantosi, Z ^{[1
]}

Greenberg, MM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 13期

关键词：

D O I：

10.1021/ja012135q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oligodeoxynucleotides containing formamidopyrimidine lesions and C-nucleoside analogues at defined sites were prepared by solid-phase synthesis and in soma oases enzymatic ligation. Formamidopyrimidine lesions were introduced as dinucleotides to prevent rearrangement to their pyranose isomers. Oligodeoxynucleotides containing single diastereomers of C-nucleoside analogues of Fady(.)dA were introduced by using the respective phosphoramidites. The formamidopyrimidine lesions reduce the T of dodecamers relative to their unmodified nucleotide counterparts when opposite the nucleotide proper base-pairing partner. However, duplexes containing Fapy(.)dG-dA mispairs melt significantly higher than those comprised of dG-dA. All duplexes containing Fapy(.)dA-dX or its C-nucleoside analogue melt lower than the respective complexes containing dA-dX. Studies of the alkaline lability of oligodeoxynucleotides containing formamidopyrimidine lesions indicate that Fapy(.)dA is readily identified as an alkali-labile lesion with use of piperidine (1.0 M, 90 degreesC, 20 min), but Fapy(.)dG is less easily identified in this manner.

引用

页码：3263 / 3269

页数：7