Azide-alkyne coupling:: A powerful reaction for bioconjugate chemistry

被引:190
作者
Breinbauer, R [1 ]
Köhn, M
机构
[1] Univ Dortmund, Fachbereich 3, D-44221 Dortmund, Germany
[2] Max Planck Inst Mol Physiol, Dept Biol Chem, D-44227 Dortmund, Germany
关键词
Alkynes; Azides; Bioconjugates; Bioorganic chemistry; Chemical biology;
D O I
10.1002/cbic.200300705
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
Tying together biological molecules is a challenge for molecular biologists and chemists. The azide-alkyne [3+2] cycloaddition has recently been introduced as a highly chemoselective ligation reaction in chemical biology. It has found application in the preparation of carbohydrate arrays, in the modification of viruses such as the capsid of the cowpea mosaic virus (CPMV; see scheme), and in the activity-based protein profiling of whole cells.
引用
收藏
页码:1147 / 1149
页数:3
相关论文
共 20 条
  • [1] Functional profiling of the proteome with affinity labels
    Campbell, DA
    Szardenings, AK
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (02) : 296 - 303
  • [2] Synthesis of sugar arrays in microtiter plate
    Fazio, F
    Bryan, MC
    Blixt, O
    Paulson, JC
    Wong, CH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) : 14397 - 14402
  • [3] Chemoselective approaches to glycoprotein assembly
    Hang, HC
    Bertozzi, CR
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (09) : 727 - 736
  • [4] Hermanson G. T., 1996, BIOCONJUGATE TECHNIQ
  • [5] Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation
    Kiick, KL
    Saxon, E
    Tirrell, DA
    Bertozzi, CR
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) : 19 - 24
  • [6] Lewis W. G., 2002, ANGEW CHEM, V114, P1095, DOI DOI 10.1002/1521-3757(20020315)114:6<1095::AID-ANGE1095>3.0.C0
  • [7] 2-3
  • [8] Lewis WG, 2002, ANGEW CHEM INT EDIT, V41, P1053, DOI 10.1002/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO
  • [9] 2-4
  • [10] Multivalent neoglycoconjugates by regiospecific cycloaddition of alkynes and azides using organic-soluble copper catalysts
    Pérez-Balderas, F
    Ortega-Muñoz, M
    Morales-Sanfrutos, J
    Hernández-Mateo, F
    Calvo-Flores, FG
    Calvo-Asín, JA
    Isac-García, J
    Santoyo-González, F
    [J]. ORGANIC LETTERS, 2003, 5 (11) : 1951 - 1954