Dendritic hydrogen bonding receptors: enantiomerically pure dendroclefts for the selective recognition of monosaccharides

被引：77

作者：

Smith, DK ^{[1
]}

Diederich, F ^{[1
]}

机构：

[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 22期

关键词：

D O I：

10.1039/a806596i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomerically pure dendritic cleft receptors (dendroclefts) with a 9,9'-spirobi[9H-fluorene] core are prepared for the recognition of glucopyranosides by I-I-bonding in CDCl(3); the enantio- and diastereo-selectivities in the complexation processes are modulated by the presence of the dendritic shell.

引用

页码：2501 / 2502

页数：2

共 18 条

[1] ENANTIOSELECTIVE COMPLEXATION OF CHIRAL DICARBOXYLIC-ACIDS IN CLEFTS OF FUNCTIONALIZED 9,9'-SPIROBIFLUORENES [J].

ALCAZAR, V ;

DIEDERICH, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (11) :1521-1523

[2] DIASTEREOSELECTIVE AND ENANTIO-SELECTIVE BINDING OF OCTYL GLUCOSIDES BY AN ARTIFICIAL RECEPTOR [J].

BHATTARAI, KM ;

BONARLAW, RP ;

DAVIS, AP ;

MURRAY, BA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) :752-754

[3] POLYOL RECOGNITION BY A STEROID-CAPPED PORPHYRIN - ENHANCEMENT AND MODULATION OF MISFIT GUEST BINDING BY ADDED WATER OR METHANOL [J].

BONARLAW, RP ;

SANDERS, JKM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :259-271

[4] MOLECULAR CLEFTS DERIVED FROM 9,9'-SPIROBI[9H-FLUORENE] FOR ENANTIOSELECTIVE COMPLEXATION OF PYRANOSIDES AND DICARBOXYLIC-ACIDS [J].

CUNTZE, J ;

OWENS, L ;

ALCAZAR, V ;

SEILER, P ;

DIEDERICH, F .

HELVETICA CHIMICA ACTA, 1995, 78 (02) :367-390

[5] A NEW CONVERGENT APPROACH TO MONODISPERSE DENDRITIC MACROMOLECULES [J].

HAWKER, CJ ;

FRECHET, JMJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (15) :1010-1013

[6] Molecular recognition of beta-ribofuranosides by synthetic polypyridine-macrocyclic receptors [J].

Inouye, M ;

Miyake, T ;

Furusyo, M ;

Nakazumi, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (50) :12416-12425

[7]

ISSBERNER J, 1994, ANGEW CHEM INT EDIT, V33, P2413

[8] Saccharide sensing with molecular receptors based on boronic acid [J].

James, TD ;

Sandanayake, KRAS ;

Shinkai, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (17) :1910-1922

[9] A saccharide 'sponge'. Synthesis and properties of a dendritic boronic acid [J].

James, TD ;

Shinmori, H ;

Takeuchi, M ;

Shinkai, S .

CHEMICAL COMMUNICATIONS, 1996, (06) :705-706

[10] HIGHLY COOPERATIVE BINDING OF ALKYL GLUCOPYRANOSIDES TO THE RESORCINOL CYCLIC TETRAMER DUE TO INTRACOMPLEX GUEST GUEST HYDROGEN-BONDING - SOLVOPHOBICITY SOLVOPHILICITY CONTROL BY AN ALKYL GROUP OF THE GEOMETRY, STOICHIOMETRY, STEREOSELECTIVITY, AND COOPERATIVITY [J].

KIKUCHI, Y ;

TANAKA, Y ;

SUTARTO, S ;

KOBAYASHI, K ;

TOI, H ;

AOYAMA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10302-10306

← 1 2 →