Supramolecular control of oligosaccharide-protein interactions: Switchable and tunable ligands for concanavalin A based on cyclodextrin

被引:47
作者
Smiljanic, Nicolas
Moreau, Vincent
Yockot, Duplex
Benito, Juan M.
Fernandez, Jose M. Garcia
Djedaini-Pilard, Florence
机构
[1] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain
[2] Univ Picardie Jules Verne, Lab Glucides, UMR 6219, F-80039 Amiens, France
关键词
carbohydrates; cyclodextrins; lectins; noncovalent interactions; receptors;
D O I
10.1002/anie.200601123
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ins and outs of binding: Supramolecular control of carbohydrate-protein interactions has been achieved through the design of β-cyclodextrin (βCD) based conjugates whose conformation is dependent on a reversible self-inclusion process. The accessibility of glycoligands to the lectin binding site is then regulated by allosteric inclusion of effector/antagonist-like molecules in the βCD cavity (see scheme). (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5465 / 5468
页数:4
相关论文
共 44 条
[1]   Structural effects of oligosaccharide-branched cyclodextrins on the dual recognition toward lectin and drug [J].
Abe, H ;
Kenmoku, A ;
Yamaguch, N ;
Hattori, K .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2002, 44 (1-4) :39-47
[2]   A RAPID NON-ACIDOLYTIC METHOD FOR DEPROTECTION AND REMOVAL OF PEPTIDES FROM SOLID-PHASE RESINS - APPLICATIONS OF AMMONIUM FORMATE CATALYTIC TRANSFER HYDROGENATION [J].
ANWER, MK ;
SPATOLA, AF .
TETRAHEDRON LETTERS, 1981, 22 (44) :4369-4372
[3]   Synthesis and biological evaluation of α-D-mannopyranoside-containing dendrimers [J].
Ashton, PR ;
Hounsell, EF ;
Jayaraman, N ;
Nilsen, TM ;
Spencer, N ;
Stoddart, JF ;
Young, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3429-3437
[4]   Cholesteryl-cyclodextrins:: synthesis and insertion into phospholipid membranes [J].
Auzély-Velty, R ;
Perly, B ;
Taché, O ;
Zemb, T ;
Jéhan, P ;
Guenot, P ;
Dalbiez, JP ;
Djedaïni-Pilard, F .
CARBOHYDRATE RESEARCH, 1999, 318 (1-4) :82-90
[5]  
Baussanne I, 2001, CHEMBIOCHEM, V2, P777, DOI 10.1002/1439-7633(20011001)2:10<777::AID-CBIC777>3.0.CO
[6]  
2-C
[7]  
Benito J. M., 2002, ANGEW CHEM, V114, P3826
[8]   Optimizing saccharide-directed molecular delivery to biological receptors:: Design, synthesis, and biological evaluation of glycodendrimer -: Cyclodextrin conjugates [J].
Benito, JM ;
Gömez-García, M ;
Mellet, CO ;
Baussanne, I ;
Defaye, J ;
Fernández, JMG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10355-10363
[9]  
Benito JM, 2002, ANGEW CHEM INT EDIT, V41, P3674, DOI 10.1002/1521-3773(20021004)41:19<3674::AID-ANIE3674>3.0.CO
[10]  
2-F