Fast copper-free click DNA ligation by the ring-strain promoted alkyne-azide cycloaddition reaction

被引:85
作者
Shelbourne, Montserrat [1 ]
Chen, Xiong [1 ]
Brown, Tom [1 ]
El-Sagheer, Afaf H. [1 ,2 ]
机构
[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
[2] Suez Canal Univ, Chem Branch, Dept Sci & Math, Fac Petr & Min Engn, Suez 43721, Egypt
关键词
SIDE-CHAINS; CHEMISTRY; FUNCTIONALIZATION; HAIRPIN; GLYCANS; (TL)DNA; ANALOG;
D O I
10.1039/c1cc10743g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Templated DNA strand ligation by the ring-strain promoted alkyne-azide [3+2] cycloaddition reaction is very fast; with dibenzocyclooctyne, the reaction is essentially complete in 1 min. It is inhibited by the presence of a single mismatched base pair suggesting applications in genetic analysis.
引用
收藏
页码:6257 / 6259
页数:3
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    Peng, Hanjing
    Draganov, Alexander Boryanov
    Huang, Zhen
    Wang, Binghe
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (12) : 3598 - 3600
  • [32] Chemically Directed Assembly of Photoactive Metal Oxide Nanoparticle Heterojunctions via the Copper-Catalyzed Azide-Alkyne Cycloaddition "Click" Reaction
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    Benson, Michelle C.
    Bishop, Lee M.
    Louis, Kacie M.
    Yeager, Joseph C.
    Tan, Yizheng
    Hamers, Robert J.
    [J]. ACS NANO, 2012, 6 (01) : 310 - 318
  • [33] Aliphatic Polyester/polyhedral Oligomeric Silsesquioxanes Hybrid Networks via Copper-free 1,3-dipolar Cycloaddition Click Reaction
    Ozdogan, Reyhan
    Daglar, Ozgun
    Durmaz, Hakan
    Tasdelen, Mehmet Atilla
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2019, 57 (22) : 2222 - 2227
  • [34] T-shaped and H-shaped polymers constructed from UV-induced strain promoted azide-alkyne cycloaddition reaction
    Zhu, Wen
    Li, Zi
    Sun, Peng
    Ren, Lixia
    Zhang, Ke
    [J]. POLYMER, 2016, 86 : 1 - 7
  • [35] One-pot synthesis of polymer monolithic column by combination of free radical polymerization and azide-alkyne cycloaddition "click" reaction and its application in capillary liquid chromatography
    Yu, Ruifang
    Hu, Wenli
    Lin, Guo
    Xiao, Qi
    Zheng, Jiangnan
    Lin, Zian
    [J]. RSC ADVANCES, 2015, 5 (13): : 9828 - 9836
  • [36] Vegetable oil-based, coumarin-containing antibacterial thermosets with improved thermal stability via copper-free thermal azide-alkyne click polymerization
    cakmakci, Emrah
    Ozdemir, Muecahit
    Sen, Ferhat
    Bulut, Mustafa
    Yalcin, Bahattin
    [J]. INDUSTRIAL CROPS AND PRODUCTS, 2022, 182
  • [37] Site-specific terminal and internal labeling of RNA by poly(A) polymerase tailing and copper-catalyzed or copper-free strain-promoted click chemistry
    Winz, Marie-Luise
    Samanta, Ayan
    Benzinger, Dirk
    Jaeschke, Andres
    [J]. NUCLEIC ACIDS RESEARCH, 2012, 40 (10)
  • [38] Cytocompatible Poly(ethylene glycol)-co-polycarbonate Hydrogels Cross-Linked by Copper-Free, Strain-Promoted Click Chemistry
    Xu, Jianwen
    Filion, Tera M.
    Prifti, Fioleda
    Song, Jie
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2730 - 2737
  • [39] Surface modification for site-directed covalent attachment of molecules via strain-promoted azide-alkyne click-chemistry reaction and photolithography
    Vrettou, Fotini
    Petrou, Panagiota
    Kakabakos, Sotirios
    Argitis, Panagiotis
    Gajos, Katarzyna
    Budkowski, Andrzej
    Chatzichristidi, Margarita
    [J]. SURFACES AND INTERFACES, 2023, 36
  • [40] Synthesis and evaluation of an 125I-labeled azide prosthetic group for efficient and bioorthogonal radiolabeling of cyclooctyne-group containing molecules using copper-free click reaction
    Choi, Mi Hee
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    Kim, Hye Rim
    Kang, Jung Ae
    Lee, Dong-Eun
    Park, Sang Hyun
    Choi, Dae Seong
    Jang, Beom-Su
    Jeon, Jongho
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (03) : 875 - 878