Non-Canonical Helical Structure of Nucleic Acids Containing Base-Modified Nucleotides

被引:13
作者
Balasubramaniyam, Thananjeyan [1 ,2 ]
Oh, Kwnag-Im [1 ,2 ]
Jin, Ho-Seong [1 ]
Ahn, Hye-Bin [1 ]
Kim, Byeong-Seon [2 ,3 ]
Lee, Joon-Hwa [1 ,2 ]
机构
[1] Gyeongsang Natl Univ, Dept Chem, Jinju 52828, Gyeongnam, South Korea
[2] Gyeongsang Natl Univ, Res Inst Nat Sci, Jinju 52828, Gyeongnam, South Korea
[3] Gyeongsang Natl Univ, Dept Chem Educ, Jinju 52828, Gyeongnam, South Korea
基金
新加坡国家研究基金会;
关键词
C8-modification; C5-modification; methylation; bromination; arylation; Z-DNA; G-quadruplex; i-motif; triplex; non-canonical DNA; CATALYZED DIRECT ARYLATION; B-Z TRANSITION; SUBSTITUTED PYRIMIDINE NUCLEOSIDES; I-MOTIF STRUCTURES; C-H ARYLATION; Z-DNA; PURINE NUCLEOSIDES; G-QUADRUPLEX; MOLECULAR-STRUCTURE; HUMAN TELOMERE;
D O I
10.3390/ijms22179552
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Chemically modified nucleobases are thought to be important for therapeutic purposes as well as diagnosing genetic diseases and have been widely involved in research fields such as molecular biology and biochemical studies. Many artificially modified nucleobases, such as methyl, halogen, and aryl modifications of purines at the C8 position and pyrimidines at the C5 position, are widely studied for their biological functions. DNA containing these modified nucleobases can form non-canonical helical structures such as Z-DNA, G-quadruplex, i-motif, and triplex. This review summarizes the synthesis of chemically modified nucleotides: (i) methylation, bromination, and arylation of purine at the C8 position and (ii) methylation, bromination, and arylation of pyrimidine at the C5 position. Additionally, we introduce the non-canonical structures of nucleic acids containing these modifications.
引用
收藏
页数:23
相关论文
共 221 条
[1]   New developments in direct functionalization of C-H and N-H bonds of purine bases via metal catalyzed cross-coupling reactions [J].
Abdoli, Morteza ;
Mirjafary, Zohreh ;
Saeidian, Hamid ;
Kakanejadifard, Ali .
RSC ADVANCES, 2015, 5 (55) :44371-44389
[2]   i-Motif DNA: structural features and significance to cell biology [J].
Abou Assi, Hala ;
Garavis, Miguel ;
Gonzalez, Carlos ;
Damha, Masad J. .
NUCLEIC ACIDS RESEARCH, 2018, 46 (16) :8038-8056
[3]   Stabilization of i-motif structures by 2′-β-fluorination of DNA [J].
Abou Assi, Hala ;
Harkness, Robert W. ;
Martin-Pintado, Nerea ;
Wilds, Christopher J. ;
Campos-Olivas, Ramon ;
Mittermaier, Anthony K. ;
Gonzalez, Carlos ;
Damha, Masad J. .
NUCLEIC ACIDS RESEARCH, 2016, 44 (11) :4998-5009
[4]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[5]   Oxidative Stress and DNA Lesions: The Role of 8-Oxoguanine Lesions in Trypanosoma cruzi Cell Viability [J].
Aguiar, Pedro H. N. ;
Furtado, Carolina ;
Repoles, Bruno M. ;
Ribeiro, Grazielle A. ;
Mendes, Isabela C. ;
Peloso, Eduardo F. ;
Gadelha, Fernanda R. ;
Macedo, Andrea M. ;
Franco, Gloria R. ;
Pena, Sergio D. J. ;
Teixeira, Santuza M. R. ;
Vieira, Leda Q. ;
Guarneri, Alessandra A. ;
Andrade, Luciana O. ;
Machado, Carlos R. .
PLOS NEGLECTED TROPICAL DISEASES, 2013, 7 (06)
[6]   Distinct 5-methylcytosine profiles in poly(A) RNA from mouse embryonic stem cells and brain [J].
Amort, Thomas ;
Rieder, Dietmar ;
Wille, Alexandra ;
Khokhlova-Cubberley, Daria ;
Riml, Christian ;
Trixl, Lukas ;
Jia, Xi-Yu ;
Micura, Ronald ;
Lusser, Alexandra .
GENOME BIOLOGY, 2017, 18
[7]   Combined use of chemically modified nucleobases and nanostructured DNA for enhanced immunostimulatory activity of CpG oligodeoxynucleotide [J].
Araie, Yuki ;
Ohtsuki, Shozo ;
Park, Soyoung ;
Nagaoka, Makoto ;
Umemura, Keisuke ;
Sugiyama, Hiroshi ;
Kusamori, Kosuke ;
Takahashi, Yuki ;
Takakura, Yoshinobu ;
Nishikawa, Makiya .
BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 29
[8]   CHEMICAL ALTERATION OF NUCLEIC-ACIDS AND THEIR COMPONENTS .13. REACTION OF NUCLEOSIDES WITH DIACYL PEROXIDES [J].
ARAKI, M ;
MAEDA, M ;
KAWAZOE, Y .
TETRAHEDRON, 1976, 32 (03) :337-340
[9]   Specific role of taurine in the 8-brominated-2′-deoxyguanosine formation [J].
Asahi, Takashi ;
Nakamura, Yoshimasa ;
Kato, Yoji ;
Osawa, Toshihiko .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2015, 586 :45-50
[10]   Chemical and Immunochemical Detection of 8-Halogenated Deoxyguanosines at Early Stage Inflammation [J].
Asahi, Takashi ;
Kondo, Hajime ;
Masuda, Mitsuharu ;
Nishino, Hoyoku ;
Aratani, Yasuaki ;
Naito, Yuji ;
Yoshikawa, Toshikazu ;
Hisaka, Shinsuke ;
Kato, Yoji ;
Osawa, Toshihiko .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (12) :9282-9291