Modification of nucleic acids using [3+2]-dipolar cycloaddition of azides and alkynes

被引:35
|
作者
Ustinov, A. V. [1 ]
Stepanova, I. A. [1 ]
Dubnyakova, V. V. [1 ]
Zatsepin, T. S. [2 ,3 ]
Nozhevnikova, E. V. [1 ]
Korshun, V. A. [1 ]
机构
[1] Russian Acad Sci, Shemyakin Ovchinnikov Inst Bioorgan Chem, Moscow 117997, Russia
[2] Moscow MV Lomonosov State Univ, Moscow, Russia
[3] Minist Publ Hlth Russia, Cent Res Inst Epidemiol, Moscow, Russia
关键词
azides; alkynes; cycloaddition; nucleic acids; oligonucleotides; modification; PHOTO-CROSS-LINKING; PHOTOLABILE OLIGODEOXYRIBONUCLEOTIDE PROBE; RUTHENIUM-CATALYZED CYCLOADDITION; SITE-SPECIFIC PHOTOMODIFICATION; MICROWAVE-ASSISTED SYNTHESIS; ESCHERICHIA-COLI RIBOSOME; TERMINAL TRIPLE BONDS; DNA-POLYMERASE-BETA; DIYNYL SIDE-CHAINS; CLICK-CHEMISTRY;
D O I
10.1134/S1068162010040011
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
The use of azide and alkyne cycloaddition reaction in the synthesis of conjugates of nucleic acids and oligodeoxyribonucleotides is reviewed. Data on the chemical and enzymatic methods for introducing azides and alkynes into DNA are summarized.
引用
收藏
页码:401 / 445
页数:45
相关论文
共 50 条
  • [1] Modification of nucleic acids using [3 + 2]-dipolar cycloaddition of azides and alkynes
    A. V. Ustinov
    I. A. Stepanova
    V. V. Dubnyakova
    T. S. Zatsepin
    E. V. Nozhevnikova
    V. A. Korshun
    [J]. Russian Journal of Bioorganic Chemistry, 2010, 36 : 401 - 445
  • [2] Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides
    Hou, Duen-Ren
    Kuan, Ting-Chun
    Li, Yu-Kai
    Lee, Richmond
    Huang, Kuo-Wei
    [J]. TETRAHEDRON, 2010, 66 (48) : 9415 - 9420
  • [3] CuO hollow nanostructures catalyze [3+2] cycloaddition of azides with terminal alkynes
    Kim, Jee Young
    Park, Ji Chan
    Kang, Hyuntae
    Song, Hyunjoon
    Park, Kang Hyun
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (03) : 439 - 441
  • [4] A CONCISE SYNTHETIC ROUTE TO CYCLOPENTENES BY [3+2]-CYCLOADDITION OF DIPOLAR TRIMETHYLENEMETHANE TO ALKYNES
    YAMAGO, S
    EJIRI, S
    NAKAMURA, E
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (19): : 2154 - 2156
  • [5] Regioselective Intramolecular Dipolar Cycloaddition of Azides and Unsymmetrical Alkynes
    Brawn, Ryan A.
    Welzel, Morgan
    Lowe, Jason T.
    Panek, James S.
    [J]. ORGANIC LETTERS, 2010, 12 (02) : 336 - 339
  • [6] A study of the scope and regioselectivity of the ruthenium-catalyzed [3+2]-cycloaddition of azides with internal alkynes
    Majireck, Max M.
    Weinreb, Steven M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22): : 8680 - 8683
  • [7] (NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and mono- or disubstituted alkynes
    Diez-Gonzalez, Silvia
    Correa, Andrea
    Cavallo, Luigi
    Nolan, Steven P.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (29) : 7558 - 7564
  • [8] APPLICATION OF HANTZSCH DIHYDROPYRIDINE IN COPPER-CATALYZED [3+2] CYCLOADDITION OF TERMINAL ALKYNES WITH AZIDES
    Jin, Zuxi
    Xue, Peng
    Fu, Enqin
    [J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (01) : 68 - 75
  • [9] [3+2]-Cycloaddition reaction of sydnones with alkynes
    Hladikova, Veronika
    Vana, Jiri
    Hanusek, Jiri
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 1317 - 1348
  • [10] [3+2]-Dipolar Cycloaddition of Nitrones to Pyrroloquinoxalinetriones
    Stepanova, E. E.
    Dmitriev, M., V
    Maslivets, A. N.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (01) : 32 - 37