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DNA photo-cross-linking using a pyranocarbazole-modified oligodeoxynucleotide with a d-threoninol linker.


ABSTRACT: An alternative photo-cross-linker having a d-threoninol skeleton instead of the 2'-deoxyribose backbone in 3-cyanovinylcarbazole (CNVK) was investigated to improve the photoreactivity of photo-cross-linkers; the photo-cross-linking rate of 3-cyanovinylcarbazole with d-threoninol (CNVD) was found to be greater than that of CNVK. Therefore, in this study, a novel photo-cross-linker having pyranocarbazole (PCX) and d-threoninol instead of the 2'-deoxyribose backbone in PCX (PCXD) was developed. The PCXD in double-stranded DNA photo-cross-linked to a pyrimidine base at the -1 position of a complementary strand similar to PCX. Furthermore, the photoreactivity of PCXD was significantly higher than that of PCX. The introduction of d-threoninol improved the reactivity of pyranocarbazole to cytosine, the use of PCXD may extend the applicability of the photo-cross-linking reaction for DNA manipulation. In particular, this novel photo-cross-linker can contribute to the photochemical regulation of gene expression or biological events in a living cell.

SUBMITTER: Fujimoto K 

PROVIDER: S-EPMC9072208 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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DNA photo-cross-linking using a pyranocarbazole-modified oligodeoxynucleotide with a d-threoninol linker.

Fujimoto Kenzo K   Yamaguchi Tsubasa T   Inatsugi Takahiro T   Takamura Masahiko M   Ishimaru Isao I   Koto Ayako A   Nakamura Shigetaka S  

RSC advances 20190927 53


An alternative photo-cross-linker having a d-threoninol skeleton instead of the 2'-deoxyribose backbone in 3-cyanovinylcarbazole (<sup>CNV</sup>K) was investigated to improve the photoreactivity of photo-cross-linkers; the photo-cross-linking rate of 3-cyanovinylcarbazole with d-threoninol (<sup>CNV</sup>D) was found to be greater than that of <sup>CNV</sup>K. Therefore, in this study, a novel photo-cross-linker having pyranocarbazole (<sup>PC</sup>X) and d-threoninol instead of the 2'-deoxyribo  ...[more]

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