Controlled Synthesis of Linear α-Cyclodextrin Oligomers Using Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition

被引:28
|
作者
Rawal, Girish K. [1 ]
Zhang, Ping [1 ]
Ling, Chang-Chun [1 ]
机构
[1] Univ Calgary, Alberta Ingenu Ctr Carbohydrate Sci, Dept Chem, Calgary, AB T2N 1N4, Canada
关键词
BETA-CYCLODEXTRIN; MOLECULAR RECOGNITION; CLICK CHEMISTRY; STRONG BINDING; DIMERS; INCLUSION; TRIMERS; ALKYNES; AZIDES;
D O I
10.1021/ol101119p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design and efficient synthesis of a novel class of linear oligomers based on cyclodextrins are described. These supramolecules have relatively rigid structures with well-defined topology and sizes, which could provide them with the ability to be used as scaffolds to present bioactive molecules to their receptors as well as host molecules.
引用
收藏
页码:3096 / 3099
页数:4
相关论文
共 50 条
  • [1] The Synthesis of a Multiblock Osteotropic Polyrotaxane by Copper(I)-Catalyzed Huisgen 1,3-Dipolar Cycloaddition
    Hein, Christopher D.
    Liu, Xin-Ming
    Chen, Fu
    Cullen, Diane M.
    Wang, Dong
    MACROMOLECULAR BIOSCIENCE, 2010, 10 (12) : 1544 - 1556
  • [2] Enantioselective Synthesis of α-Heteroarylpyrrolidines by Copper-Catalyzed 1,3-Dipolar Cycloaddition of α-Silylimines
    Pascual-Escudero, Ana
    Gonzalez-Esguevillas, Maria
    Padilla, Silvia
    Adrio, Javier
    Carretero, Juan C.
    ORGANIC LETTERS, 2014, 16 (08) : 2228 - 2231
  • [3] Efficient synthesis of linear multifunctional poly(ethylene glycol) by copper(I)-catalyzed huisgen 1,3-dipolar cycloaddition
    Liu, Xin-Ming
    Thakur, Ashish
    Wang, Dong
    BIOMACROMOLECULES, 2007, 8 (09) : 2653 - 2658
  • [4] Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition
    Ward, Sandra
    Ling, Chang-Chun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (25) : 4853 - 4861
  • [5] Synthesis of new azido porphyrins and their reactivity in copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction with alkynes
    Severac, Marjorie
    Le Pleux, Loic
    Scarpaci, Annabelle
    Blart, Errol
    Odobel, Fabrice
    TETRAHEDRON LETTERS, 2007, 48 (37) : 6518 - 6522
  • [6] The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition
    Breugst, Martin
    Reissig, Hans-Ulrich
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (30) : 12293 - 12307
  • [7] Thiophene-based donor-acceptor co-oligomers by copper-catalyzed 1,3-dipolar cycloaddition
    Potratz, Stefanie
    Mishra, Amaresh
    Baeuerle, Peter
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 683 - 692
  • [8] Beyond copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition: Synthesis and mechanism insights
    Gomes, Roberto S.
    Jardim, Guilherme A. M.
    de Carvalho, Renato L.
    Araujo, Maria H.
    da Silva Junior, Eufranio N.
    TETRAHEDRON, 2019, 75 (27) : 3697 - 3712
  • [9] Conjugation of Phenothiazine and Substituted Indoles via Copper-Catalyzed 1,3-Dipolar Cycloaddition
    Sokolov, V. B.
    Aksinenko, A. Yu.
    Goreva, T. V.
    Epishina, T. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (07) : 1546 - 1549
  • [10] Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Unsaturated Sultones
    Furuya, Shohei
    Kanemoto, Kazuya
    Fukuzawa, Shin-ichi
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 8142 - 8148