Double helical oligoresorcinols specifically recognize oligosaccharides via heteroduplex formation through noncovalent interactions in water

被引：103

作者：

Goto, Hidetoshi

Furusho, Yoshio ^{[1
]}

Yashima, Eiji

机构：

[1] JST, ERATO, Yashima Super Struct Helix Project, Moriyama Ku, Nagoya, Aichi 4630003, Japan

[2] Nagoya Univ, Inst Adv Res, Nagoya, Aichi 4648603, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 29期

关键词：

D O I：

10.1021/ja0730359

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report on the oligosaccharide recognition through noncovalent interactions in water based on a unique supramolecular homoduplex-to-heteroduplex transformation of the oligoresorcinol nonamer as a fully artificial receptor. The oligoresorcinol forms a double helix in water, which unravels and entwines upon complexation with specific oligosaccharides with a particular chain length and glucosidic linkage pattern, thus generating the heteroduplex with an excess one-handed helical conformation that can be readily monitored and further quantified by absorption, circular dichroism, and NMR spectroscopies.

引用

收藏

页码：9168 / 9174

页数：7

相关论文

共 95 条

[1] A rigid C3v-symmetrical host for saccharide recognition:: 1,3,5-tris(2-hydroxyaryl)-2,4,6-trimethylbenzenes [J].

Abe, H ;

Aoyagi, Y ;

Inouye, M .

ORGANIC LETTERS, 2005, 7 (01) :59-61

[2] Lanthanide complexes as fluorescent indicators for neutral sugars and cancer biomarkers [J].

Alpturk, Onur ;

Rusin, Oleksandr ;

Fakayode, Sayo O. ;

Wang, Weihua ;

Escobedo, Jorge O. ;

Warner, Isiah M. ;

Crowe, William E. ;

Kral, Vladimir ;

Pruet, Jeff M. ;

Strongin, Robert M. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (26) :9756-9760

[3] A NEW FAMILY OF CHIRAL BINAPHTHYL-DERIVED CYCLOPHANE RECEPTORS - COMPLEXATION OF PYRANOSIDES [J].

ANDERSON, S ;

NEIDLEIN, U ;

GRAMLICH, V ;

DIEDERICH, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1596-1600

[4] POLAR HOST GUEST INTERACTION - BINDING OF NONIONIC POLAR COMPOUNDS WITH A RESORCINOL-ALDEHYDE CYCLOOLIGOMER AS A LIPOPHILIC POLAR HOST [J].

AOYAMA, Y ;

TANAKA, Y ;

TOI, H ;

OGOSHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :634-635

[5] Carbohydrate-based receptors with multiple thiourea binding sites.: Multipoint hydrogen bond recognition of dicarboxylates and monosaccharides [J].

Benito, JM ;

Gómez-García, M ;

Blanco, JLJ ;

Mellet, CO ;

Fernández, JMG .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1366-1372

[6]

BEZTOZZI CR, 2001, SCIENCE, V291, P2357

[7] 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

[8] Cyclic hexapeptides with free carboxylate groups as new receptors for monosaccharides [J].

Bitta, J ;

Kubik, S .

ORGANIC LETTERS, 2001, 3 (17) :2637-2640

[9] ARTIFICIAL RECEPTORS FOR CARBOHYDRATE-DERIVATIVES [J].

BONARLAW, RP ;

DAVIS, AP ;

MURRAY, BA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1407-1408

[10] 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

← 1 2 3 4 5 6 7 8 9 10 →