Folding of a β-cyclodextrin monosubstituted at its secondary face, revealed by NMR studies of local structural variations

被引：8

作者：

Berthault, P

Birlirakis, N

机构：

[1] CNRS, Inst Chim Subst Nat, Lab RMN, F-91198 Gif Sur Yvette, France

[2] Ctr Etud Saclay, CEA, Serv Chim Mol, Lab Commun RMN, F-91191 Gif Sur Yvette, France

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)00217-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The H-1 NMR study of a CD mono-functionalized at its secondary face is presented. It is shown that mono-(3-Tyr-3-deoxy-altro)-beta-CD undergoes a solvent-dependent conformational change. Passing from organic medium to water, a stable self-inclusion complex is formed. Such a folding is accompanied by a local structural modification of the substituted altrose ring, which can be easily detected from the important variation of its H1-H2 coupling constant. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2463 / 2469

页数：7

相关论文

共 19 条

[1] A SELF-INCLUDED CYCLOMALTOHEPTAOSE DERIVATIVE STUDIED BY NMR-SPECTROSCOPY AND MOLECULAR MODELING [J].

BERTHAULT, P ;

DUCHESNE, D ;

DESVAUX, H ;

GILQUIN, B .

CARBOHYDRATE RESEARCH, 1995, 276 (02) :267-287

[2] MIMICS OF TRANSAMINASE ENZYMES [J].

BRESLOW, R ;

CZARNIK, AW ;

LAUER, M ;

LEPPKES, R ;

WINKLER, J ;

ZIMMERMAN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :1969-1979

[3] IMPROVED VERSIONS OF OFF-RESONANCE ROESY [J].

DESVAUX, H ;

BERTHAULT, P ;

BIRLIRAKIS, N ;

GOLDMAN, M ;

PIOTTO, M .

JOURNAL OF MAGNETIC RESONANCE SERIES A, 1995, 113 (01) :47-52

[4] CONFORMATION FOR A BETA-CYCLODEXTRIN MONOSUBSTITUTED WITH A CYCLIC DIPEPTIDE [J].

DIBLASIO, B ;

PAVONE, V ;

NASTRI, F ;

ISERNIA, C ;

SAVIANO, M ;

PEDONE, C ;

CUCINOTTA, V ;

IMPELLIZZERI, G ;

RIZZARELLI, E ;

VECCHIO, G .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (15) :7218-7221

[5] POTENTIAL FORMATION OF INTRAMOLECULAR INCLUSION COMPLEXES IN PEPTIDO-CYCLODEXTRINS AS EVIDENCED BY NMR-SPECTROSCOPY [J].

DJEDAINIPILARD, F ;

AZAROUALBELLANGER, N ;

GOSNAT, M ;

VERNET, D ;

PERLY, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (04) :723-730

[6]

DUNBAR RA, 1994, SUPRAMOL CHEM, V3, P93

[7] Molecular modeling of saccharides, part 20 -: Guest-induced conformational change in a flexible host:: mono-altro-β-cyclodextrin [J].

Fujita, K ;

Chen, WH ;

Yuan, DQ ;

Nogami, Y ;

Koga, T ;

Fujioka, T ;

Mihashi, K ;

Immel, S ;

Lichtenthaler, FW .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1689-1696

[8] MODIFICATIONS OF THE SECONDARY HYDROXYL SIDE OF ALPHA-CYCLODEXTRIN AND NMR-STUDIES OF THEM [J].

IKEDA, H ;

NAGANO, Y ;

DU, YQ ;

IKEDA, T ;

TODA, F .

TETRAHEDRON LETTERS, 1990, 31 (35) :5045-5048

[9]

Immel S, 1999, CHEM-EUR J, V5, P3185, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3185::AID-CHEM3185>3.0.CO

[10]

2-W