Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril

被引：28

作者：

Berbeci, Lidia Strimbu ^{[1
,2
]}

Wang, Wei ^{[1
,2
]}

Kaifer, Angel E. ^{[1
,2
]}

机构：

[1] Univ Miami, Ctr Supramol Sci, Coral Gables, FL 33124 USA

[2] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 17期

关键词：

D O I：

10.1021/ol8013667

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The cucurbit[6]uril (CB6) host forms stable complexes with 2-aminoethanethiol (cysteamine) and a derivative that contains a bulky terminal group attached to the amine group, as well as with the related disulfide cystamine. In these complexes, the thiol or the disulfide group is encapsulated inside the host cavity. The CB6-complexed thiols show drastically decreased reactivity with several oxidants, while the C136-bound disulfide also exhibits hindered reactivity with reducing agents, such as dithiothreitol.

引用

页码：3721 / 3724

页数：4

共 18 条

[1]

Structure and binding properties of water-soluble cavitands and capsules [J].

Biros, Shannon M. ;

Rebek, Julius, Jr. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (01) :93-104

[2]

Effective molarities in supramolecular catalysis of two-substrate reactions [J].

Cacciapaglia, R ;

Di Stefano, S ;

Mandolini, L .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :113-122

[3]

CRAM DJ, 1991, ANGEW CHEM INT EDIT, V30, P1024, DOI 10.1002/anie.199110241

[4]

The role of thiols and disulfides in platelet function [J].

Essex, DW .

ANTIOXIDANTS & REDOX SIGNALING, 2004, 6 (04) :736-746

[5]

Gilbert H.F., 1990, ADV ENZYMOL RAMB, V63, P69

[6]

Redefining oxidative stress [J].

Jones, Dean P. .

ANTIOXIDANTS & REDOX SIGNALING, 2006, 8 (9-10) :1865-1879

[7]

INTERMEDIATES IN THE FOLDING REACTIONS OF SMALL PROTEINS [J].

KIM, PS ;

BALDWIN, RL .

ANNUAL REVIEW OF BIOCHEMISTRY, 1990, 59 :631-660

[8]

Supramolecular assemblies built with host-stabilized charge-transfer interactions [J].

Ko, Young Ho ;

Kim, Eunju ;

Hwang, Ilha ;

Kim, Kimoon .

CHEMICAL COMMUNICATIONS, 2007, (13) :1305-1315

[9]

Allosteric supramolecular receptors and catalysts [J].

Kovbasyuk, L ;

Krämer, R .

CHEMICAL REVIEWS, 2004, 104 (06) :3161-3187

[10]

The cucurbit[n]uril family [J].

Lagona, J ;

Mukhopadhyay, P ;

Chakrabarti, S ;

Isaacs, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (31) :4844-4870

← 1 2 →