DNA Photo-Cross-Linking Using 3-Cyanovinylcarbazole Modified Oligonucleotide with Threoninol Linker

被引:35
|
作者
Sakamoto, Takashi [1 ]
Tanaka, Yuya [1 ]
Fujimoto, Kenzo [1 ,2 ]
机构
[1] Japan Adv Inst Sci & Technol, Sch Mat Sci, Nomi, Ishikawa 9231292, Japan
[2] Japan Adv Inst Sci & Technol, Res Ctr Bioarchitecture, Nomi, Ishikawa 9231292, Japan
关键词
POINT MUTATIONS; DOUBLE-STRAND; RNA; METHYLPHOSPHONATES; NUCLEOSIDE; DERIVATIVES; TRANSITION; TRIPLEX; QUICK;
D O I
10.1021/acs.orglett.5b00035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Cyanovinylcarbazole modified d-threoninol (D-CNV) was incorporated in oligodeoxyribonucleotide and tested for a photo-cross-linking reaction with complementary oligodeoxyribonucleotide. The photoreactivity was 1.8- to 8-fold greater than that of 3-cyanovinylcarbazole modified deoxyribose (K-CNV) previously reported. From the results of melting analysis and circular dichroism spectroscopy of the duplexes, the relatively flexible structure of D-CNV compared with K-CNV might be advantageous for [2 + 2] photocycloaddition between the cyanovinyl group on the D-CNV and pyrimidine base in the complementary strand.
引用
收藏
页码:936 / 939
页数:4
相关论文
共 50 条
  • [1] Double duplex invasion of DNA induced by ultrafast photo-cross-linking using 3-cyanovinylcarbazole for antigene methods
    Nakamura, Shigetaka
    Kawabata, Hayato
    Fujimoto, Kenzo
    CHEMICAL COMMUNICATIONS, 2017, 53 (54) : 7616 - 7619
  • [2] DNA photo-cross-linking using a pyranocarbazole-modified oligodeoxynucleotide with a D-threoninol linker
    Fujimoto, Kenzo
    Yamaguchi, Tsubasa
    Inatsugi, Takahiro
    Takamura, Masahiko
    Ishimaru, Isao
    Koto, Ayako
    Nakamura, Shigetaka
    RSC ADVANCES, 2019, 9 (53) : 30693 - 30697
  • [3] Critical Effect of Base Pairing of Target Pyrimidine on the Interstrand Photo-Cross-Linking of DNA via 3-Cyanovinylcarbazole Nucleoside
    Sakamoto, Takashi
    Ooe, Minako
    Fujimoto, Kenzo
    BIOCONJUGATE CHEMISTRY, 2015, 26 (08) : 1475 - 1478
  • [4] Effect of nucleobase change on cytosine deamination through DNA photo-cross-linking reaction via 3-cyanovinylcarbazole nucleoside
    Sethi, Siddhant
    Ooe, Minako
    Sakamoto, Takashi
    Fujimoto, Kenzo
    MOLECULAR BIOSYSTEMS, 2017, 13 (06) : 1152 - 1156
  • [5] Photo-cross-linking using trifluorothymidine and 3-cyanovinylcarbazole induced a large shifted 19F MR signal
    Nakamura, Shigetaka
    Fujimoto, Kenzo
    CHEMICAL COMMUNICATIONS, 2015, 51 (59) : 11765 - 11768
  • [6] Reversible photo-cross-linking of the GCN4 peptide containing 3-cyanovinylcarbazole amino acid to double-stranded DNA
    Qiu, Zhiyong
    Nakamura, Shigetaka
    Fujimoto, Kenzo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) : 6277 - 6283
  • [7] Details of the Ultrafast DNA Photo-Cross-Linking Reaction of 3-Cyanovinylcarbazole Nucleoside: Cis-Trans Isomeric Effect and the Application for SNP-Based Genotyping
    Fujimoto, Kenzo
    Yamada, Asuka
    Yoshimura, Yoshinaga
    Tsukaguch, Tadashi
    Sakamoto, Takashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) : 16161 - 16167
  • [9] RNA fluorescence in situ hybridization using 3-cyanovinylcarbazole modified oligodeoxyribonucleotides as photo-cross-linkable probes
    Fujimoto, Kenzo
    Toyosato, Kei
    Nakamura, Shigetaka
    Sakamoto, Takashi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (21) : 5312 - 5314
  • [10] Reversible cyanovinylcarbazole-based polymer gel via photo-cross-linking reaction
    Cha, Yubin
    Choi, Yeonweon
    Choi, Heekyoung
    Park, Hyesong
    Kim, Ju Hyun
    Jung, Jong Hwa
    SUPRAMOLECULAR CHEMISTRY, 2018, 30 (03) : 227 - 233