Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry

被引:225
作者
Kumar, Ravindra
El-Sagheer, Afaf
Tumpane, John
Lincoln, Per
Wilhelmsson, L. Marcus
Brown, Tom [1 ]
机构
[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
[2] Chalmers, Dept Chem & Biol Engn Phys Chem, SE-41296 Gothenburg, Sweden
关键词
D O I
10.1021/ja070273v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalyzed azide-alkyne cycloaddition reaction has been used for the template-mediated chemical ligation of two oligonucleotide strands, one with a 5'-alkyne and the other with a 3'-azide, to produce a DNA strand with an unnatural backbone at the ligation point. A template-free click-ligation reaction has been used for the intramolecular circularization of a single stranded oligonucleotide which was used as a template for the synthesis of a covalently closed DNA catenane.
引用
收藏
页码:6859 / 6864
页数:6
相关论文
共 21 条
  • [1] Sequential self-assembly of a DNA hexagon as a template for the organization of gold nanoparticles
    Aldaye, FA
    Sleiman, HF
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) : 2204 - 2209
  • [2] CHEMOSELECTIVITY OF THE REACTION OF DICHLOROBORANES WITH FUNCTIONAL AZIDES - EFFICIENT FUNCTIONALIZED SECONDARY AMINE SYNTHESIS
    CARBONI, B
    VAULTIER, M
    CARRIE, R
    [J]. TETRAHEDRON, 1987, 43 (08) : 1799 - 1810
  • [3] Polytriazoles as copper(I)-stabilizing ligands in catalysis
    Chan, TR
    Hilgraf, R
    Sharpless, KB
    Fokin, VV
    [J]. ORGANIC LETTERS, 2004, 6 (17) : 2853 - 2855
  • [4] Clicking functionality onto electrode surfaces
    Collman, JP
    Devaraj, NK
    Chidsey, CED
    [J]. LANGMUIR, 2004, 20 (04) : 1051 - 1053
  • [5] Template-directed photoreversible ligation of deoxyoligonucleotides via 5-vinyldeoxyuridine
    Fujimoto, K
    Matsuda, S
    Takahashi, N
    Saito, I
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) : 5646 - 5647
  • [6] Template-directed reversible photocircularization of DNA via 5-vinyldeoxycytidine
    Fujimoto, K
    Matsuda, S
    Ogawa, N
    Hayashi, M
    Saito, I
    [J]. TETRAHEDRON LETTERS, 2000, 41 (33) : 6451 - 6454
  • [7] Reaction discovery enabled by DNA-templated synthesis and in vitro selection
    Kanan, MW
    Rozenman, MM
    Sakurai, K
    Snyder, TM
    Liu, DR
    [J]. NATURE, 2004, 431 (7008) : 545 - 549
  • [8] Recognition of DNA, RNA, and proteins by circular oligonucleotides
    Kool, ET
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (08) : 502 - 510
  • [9] Kool ET, 1996, ANNU REV BIOPH BIOM, V25, P1
  • [10] Langley GJ, 1999, RAPID COMMUN MASS SP, V13, P1717, DOI 10.1002/(SICI)1097-0231(19990915)13:17<1717::AID-RCM704>3.3.CO