Cucurbit[n]urils: from mechanism to structure and function

被引:382
作者
Isaacs, Lyle [1 ]
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
关键词
HOST-GUEST COMPLEXATION; GLYCOLURIL DIMERS; DIASTEREOSELECTIVE FORMATION; CUCURBITURIL HOMOLOGS; MOLECULAR CLIPS; PK(A) SHIFTS; BINDING; STABILIZATION; ENCAPSULATION; RECOGNITION;
D O I
10.1039/b814897j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This feature article details some of the unusual recognition properties of the cucurbit[n]uril family (CB[n]) of molecular containers. It discusses the mechanism of CB[ n] formation, which proceeds from glycoluril via methylene bridged glycoluril oligomers, along with descriptions of the structures and recognition properties of some kinetically stable macrocyclic intermediates along the way. These partially formed CB[n]-type receptors known as nor-seco-CB[n] display intriguing properties such as chiral recognition, homotropic allostery, and function as aldehyde reaction cucurbituril synthons.
引用
收藏
页码:619 / 629
页数:11
相关论文
共 61 条
[1]   Supramolecular tandem enzyme assays for multiparameter sensor arrays and enantiomeric excess determination of amino acids [J].
Bailey, David M. ;
Hennig, Andreas ;
Uzunova, Vanya D. ;
Nau, Werner M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (20) :6069-6077
[2]   Cucurbituril binding of trans-[{PtCl(NH3)2}2(μ-NH2(CH2)8NH2)]2+ and the effect on the reaction with cysteine [J].
Bali, Mark S. ;
Buck, Damian P. ;
Coe, Andrew J. ;
Day, Anthony I. ;
Collins, J. Grant .
DALTON TRANSACTIONS, 2006, (45) :5337-5344
[3]   Thermodynamic data for complex formation between cucurbituril and alkali and alkaline earth cations in aqueous formic acid solution [J].
Buschmann, HJ ;
Jansen, K ;
Meschke, C ;
Schollmeyer, E .
JOURNAL OF SOLUTION CHEMISTRY, 1998, 27 (02) :135-140
[4]   Reconfigurable four-component molecular switch based on pH-controlled guest swapping [J].
Chakrabarti, Sriparna ;
Mukhopadhyay, Pritam ;
Lin, Shirley ;
Isaacs, Lyle .
ORGANIC LETTERS, 2007, 9 (12) :2349-2352
[5]   Diastereoselective formation of glycoluril dimers:: Isomerization mechanism and implications for cucurbit[n]uril synthesis [J].
Chakraborty, A ;
Xu, AX ;
Witt, D ;
Lagona, J ;
Fettinger, JC ;
Isaacs, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8297-8306
[6]   HOST-GUEST COMPLEXATION .63. CONSTRICTIVE AND INTRINSIC BINDING IN A HEMICARCERAND CONTAINING 4 PORTALS [J].
CRAM, DJ ;
BLANDA, MT ;
PAEK, K ;
KNOBLER, CB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7765-7773
[7]   HOST-GUEST COMPLEXATION .58. GUEST RELEASE AND CAPTURE BY HEMICARCERANDS INTRODUCES THE PHENOMENON OF CONSTRICTIVE BINDING [J].
CRAM, DJ ;
TANNER, ME ;
KNOBLER, CB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7717-7727
[8]   Controlling factors in the synthesis of cucurbituril and its homologues [J].
Day, A ;
Arnold, AP ;
Blanch, RJ ;
Snushall, B .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8094-8100
[9]  
Day AI, 2002, ANGEW CHEM INT EDIT, V41, P275, DOI 10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO
[10]  
2-M