Rotaxanes and Biofunctionalized Pseudorotaxanes via Thiol-Maleimide Click Chemistry

被引：17
作者：
Choudhary, Umesh [1 ]
Northrop, Brian H. [1 ]
机构：
[1] Wesleyan Univ, Dept Chem, Middletown, CT 06459 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 08期
关键词：
CROWN-ETHERS; DONOR; MACHINES; INTERLOCKING; DERIVATIVES; COMPONENTS; SHUTTLES; COMPLEX;
D O I：
10.1021/ol300614z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Base-catalyzed thiol-maleimide click chemistry has been applied to the synthesis of neutral donor-acceptor [2]rotaxanes in good yield. This method is extended further to the synthesis of a glutathione-functionalized [2]pseudorotaxane, a precursor to integrated conjugates of interlocked molecules with proteins and enzymes.
引用
收藏
页码：2082 / 2085
页数：4
相关论文
共 52 条
  • [1] [Anonymous], 2000, Templated organic synthesis
  • [2] The slipping approach to self-assembling [n]rotaxanes
    Asakawa, M
    Ashton, PR
    Ballardini, R
    Balzani, V
    Belohradsky, M
    Gandolfi, MT
    Kocian, O
    Prodi, L
    Raymo, FM
    Stoddart, JF
    Venturi, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (02) : 302 - 310
  • [3] Acid-base controllable molecular shuttles
    Ashton, PR
    Ballardini, R
    Balzani, V
    Baxter, I
    Credi, A
    Fyfe, MCT
    Gandolfi, MT
    Gómez-López, M
    Martínez-Díaz, MV
    Piersanti, A
    Spencer, N
    Stoddart, JF
    Venturi, M
    White, AJP
    Williams, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) : 11932 - 11942
  • [4] Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures
    Aucagne, V
    Hänni, KD
    Leigh, DA
    Lusby, PJ
    Walker, DB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) : 2186 - 2187
  • [5] A molecular elevator
    Badjic, JD
    Balzani, V
    Credi, A
    Silvi, S
    Stoddart, JF
    [J]. SCIENCE, 2004, 303 (5665) : 1845 - 1849
  • [6] Simple molecular machines: Chemically driven unthreading and rethreading of a [2]pseudorotaxane
    Ballardini, R
    Balzani, V
    Credi, A
    Gandolfi, MT
    Langford, SJ
    Menzer, S
    Prodi, L
    Stoddart, JF
    Venturi, M
    Williams, DJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (09) : 978 - 981
  • [7] A BRIEF SURVEY OF METHODS FOR PREPARING PROTEIN CONJUGATES WITH DYES, HAPTENS, AND CROSS-LINKING REAGENTS
    BRINKLEY, M
    [J]. BIOCONJUGATE CHEMISTRY, 1992, 3 (01) : 2 - 13
  • [8] First considerations: Principles, classification, and history
    Busch, DH
    [J]. TEMPLATES IN CHEMISTRY II, 2005, 249 : 1 - 65
  • [9] An Approach to Thermodynamically Controlled Supramolecular Assembly Possessing an Integral Locking Mechanism
    Cagulada, Amy M.
    Hamilton, Darren G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (03) : 902 - +
  • [10] Probing Donor-Acceptor Interactions and Co-Conformational Changes in Redox Active Desymmetrized [2]Catenanes
    Cao, Dennis
    Amelia, Matteo
    Klivansky, Liana M.
    Koshkakaryan, Gayane
    Khan, Saeed I.
    Semeraro, Monica
    Silvi, Serena
    Venturi, Margherita
    Credi, Alberto
    Liu, Yi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) : 1110 - 1122
123456