Recent applications of the CuI-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry

被引:225
作者
Dedola, Simone
Nepogodiev, Sergey A.
Field, Robert A. [1 ]
机构
[1] Univ E Anglia, Sch Chem Sci & Pharm, Norwich NR4 7TJ, Norfolk, England
[2] John Innes Ctr Plant Sci Res, Dept Biol Chem, Norwich NR4 7UH, Norfolk, England
基金
英国生物技术与生命科学研究理事会;
关键词
D O I
10.1039/b618048p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This article surveys recent applications of Cu-I-catalysed 1,3-dipolar cycloaddition of azides and alkynes in carbohydrate chemistry, highlighting developments in the preparation of simple glycoside and oligosaccharide mimetics, glyco-macrocycles, glycopeptides, glyco-clusters and carbohydrate arrays.
引用
收藏
页码:1006 / 1017
页数:12
相关论文
共 83 条
  • [1] A comparative study of bioorthogonal reactions with azides
    Agard, Nicholas J.
    Baskin, Jeremy M.
    Prescher, Jennifer A.
    Lo, Anderson
    Bertozzi, Carolyn R.
    [J]. ACS CHEMICAL BIOLOGY, 2006, 1 (10) : 644 - 648
  • [2] Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition
    Agren, Jenny K. M.
    Billing, Johan F.
    Grundberg, Hans E.
    Nilsson, Ulf J.
    [J]. SYNTHESIS-STUTTGART, 2006, 18 (18): : 3141 - 3145
  • [3] Akula RA, 2004, HETEROCYCLES, V63, P2719
  • [4] Click chemistry to functionalise peptidomimetics
    Arosio, Daniela
    Bertoli, Matteo
    Manzoni, Leonardo
    Scolastico, Carlo
    [J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3697 - 3700
  • [5] C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles
    Billing, JF
    Nilsson, UJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) : 4847 - 4850
  • [6] Azide/alkyne-"click" reactions: Applications in material science and organic synthesis
    Binder, Wolfgang H.
    Kluger, Christian
    [J]. CURRENT ORGANIC CHEMISTRY, 2006, 10 (14) : 1791 - 1815
  • [7] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective
    Bock, VD
    Hiemstra, H
    van Maarseveen, JH
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 51 - 68
  • [8] Highly convergent synthesis of C3- or C2-symmetric carbohydrate macrocycles
    Bodine, KD
    Gin, DY
    Gin, MS
    [J]. ORGANIC LETTERS, 2005, 7 (20) : 4479 - 4482
  • [9] Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide
    Bodine, KD
    Gin, DY
    Gin, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) : 1638 - 1639
  • [10] Microwave assisted "click" chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support
    Bouillon, Camille
    Meyer, Albert
    Vidal, Sebastien
    Jochum, Anne
    Chevolot, Yann
    Cloarec, Jean-Pierre
    Praly, Jean-Pierre
    Vasseur, Jean-Jacques
    Morvan, Francois
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12) : 4700 - 4702