Diastereoselective amplification of an induced-fit receptor from a dynamic combinatorial library

被引：112

作者：

Corbett, PT ^{[1
]}

Tong, LH ^{[1
]}

Sanders, JKM ^{[1
]}

Otto, S ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 25期

关键词：

D O I：

10.1021/ja050790i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A high-affinity, induced-fit receptor for NMe4I was discovered using dynamic combinatorial chemistry. The addition of the guest to a dynamic combinatorial library made using a racemic mixture of chiral building blocks caused the strong and highly diastereoselective amplification of the receptor at the expense of other library components. The receptor and its mode of binding were characterized by NMR, ITC, and re-equilibration experiments, from which it was deduced that the receptor probably forms a folded four-stave barrel shape on binding of the guest. Copyright © 2005 American Chemical Society.

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页码：8902 / 8903

页数：2

相关论文

共 21 条

[1] Entropic origin of the sulfonate groups' electrostatic assistance in the complexation of quaternary ammonium cations by water soluble calix[4]arenes [J].

Arena, G ;

Casnati, A ;

Contino, A ;

Gulino, FG ;

Sciotto, D ;

Ungaro, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (03) :419-423

[2] Selection and amplification of a catalyst from a dynamic combinatorial library [J].

Brisig, B ;

Sanders, JKM ;

Otto, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (11) :1270-1273

[3] Use of molecular recognition to drive chemical evolution .1. Controlling the composition of an equilibrating mixture of simple arginine receptors [J].

Eliseev, AV ;

Nelen, MI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :1147-1148

[4] Amplification of dynamic chiral crown ether complexes during cyclic acetal formation [J].

Fuchs, B ;

Nelson, A ;

Star, A ;

Stoddart, JF ;

Vidal, SB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4220-4224

[5] Molecular amplification in a dynamic system by ammonium cations [J].

Furlan, RLE ;

Ng, YF ;

Cousins, GRL ;

Redman, JE ;

Sanders, JKM .

TETRAHEDRON, 2002, 58 (04) :771-778

[6] Selective host amplification from a dynamic combinatorial library of oligoimines for the syntheses of different optically active polyazamacrocycles [J].

González-Alvarez, A ;

Alfonso, I ;

López-Ortiz, F ;

Aguirre, A ;

García-Granda, S ;

Gotor, V .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (05) :1117-1127

[7] Chemical evolution: A model system that selects and amplifies a receptor for the tripeptide (D)Pro(L)Val(D)Val [J].

Hioki, H ;

Still, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :904-905

[8] MOLECULAR RECOGNITION IN AQUEOUS-MEDIA - NEW BINDING-STUDIES PROVIDE FURTHER INSIGHTS INTO THE CATION-PI INTERACTION AND RELATED PHENOMENA [J].

KEARNEY, PC ;

MIZOUE, LS ;

KUMPF, RA ;

FORMAN, JE ;

MCCURDY, A ;

DOUGHERTY, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9907-9919

[9]

Kusukawa T, 2001, ANGEW CHEM INT EDIT, V40, P1879

[10] A selective receptor for arginine derivatives in aqueous media. Energetic consequences of salt bridges that are highly exposed to water [J].

Ngola, SM ;

Kearney, PC ;

Mecozzi, S ;

Russell, K ;

Dougherty, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (06) :1192-1201