β-Cyclodextrin-Glycerol Dimers: Synthesis and NMR Conformational Analysis

被引：16

作者：

Legros, Vanessa ^{[1
]}

Vanhaverbeke, Cecile ^{[2
]}

Souard, Florence ^{[2
]}

Len, Christophe ^{[3
]}

Desire, Jerome ^{[1
]}

机构：

[1] Univ Poitiers, CNRS, Inst Chim Milieux & Mat Poitiers, UMR 7285, F-86022 Poitiers, France

[2] Univ Grenoble 1, CNRS, Dept Pharmacochim Mol, ICMG FR 2607,UMR 5063, F-38041 Grenoble, France

[3] Univ Technol Compiegne, ESCOM, EA 4297, Ctr Rech Royallieu, F-60205 Compiegne, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 13期

关键词：

Cyclodextrins; Glycerol; Click chemistry; Conformation analysis; COOPERATIVE BINDING; ALPHA; INCLUSION; CHEMISTRY; BEHAVIOR; ACCESS;

D O I：

10.1002/ejoc.201201716

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of new -cyclodextrin dimers linked through their primary faces by different glycerol-like moieties by click chemistry is described. The unusual behaviour of these cyclodextringlycerol dimers in aqueous solution has been studied by NMR spectroscopy. We show that, depending on the length of the linking arm between the two cyclodextrins, the dimers could adopt very different conformations in water: symmetrical or pseudo[1]rotaxane-like structures through one D-glucopyranose unit tumbling in one -cyclodextrin.

引用

页码：2583 / 2590

页数：8

共 44 条

[1] New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands [J].

Aime, Silvio ;

Gianolio, Eliana ;

Arena, Francesca ;

Barge, Alessandro ;

Martina, Katia ;

Heropoulos, George ;

Cravotto, Giancarlo .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (02) :370-379

[2]

[Anonymous], 1998, Chem. Rev, P98

[3] A review on the use of cyclodextrins in foods [J].

Astray, G. ;

Gonzalez-Barreiro, C. ;

Mejuto, J. C. ;

Rial-Otero, R. ;

Simal-Gandara, J. .

FOOD HYDROCOLLOIDS, 2009, 23 (07) :1631-1640

[4]

Atwood J.L., 1996, COMPREHENSIVE SUPRAM

[5] Synthesis and pharmacological evaluation of a new targeted drug carrier system:: β-Cyclodextrin coupled to oxytocin [J].

Bertolla, Carine ;

Rolin, Stephanie ;

Evrard, Brigitte ;

Pochet, Lionel ;

Masereel, Bernard .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (06) :1855-1858

[6] Analytical and preparative enantioseparation of DL-penicillamine and DL-cysteine by high-performance liquid chromatography on α-acid glycoprotein and β-cyclodextrin columns using ninhydrin as a reversible tagging reagent [J].

Bhushan, Ravi ;

Kumar, Rajender .

JOURNAL OF CHROMATOGRAPHY A, 2009, 1216 (15) :3413-3417

[7] Artificial enzymes, "Chemzymes": current state and perspectives [J].

Bjerre, Jeannette ;

Rousseau, Cyril ;

Marinescu, Lavinia ;

Bols, Mikael .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2008, 81 (01) :1-11

[8] Sulfobutyl ether-β-cyclodextrins:: Promising supramolecular carriers for aqueous organometallic catalysis [J].

Blach, P ;

Landy, D ;

Fourmentin, S ;

Surpateanu, G ;

Bricout, H ;

Ponchel, A ;

Hapiot, F ;

Monflier, E .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (09) :1301-1307

[9] VERY STRONG BINDING OF APPROPRIATE SUBSTRATES BY CYCLODEXTRIN DIMERS [J].

BRESLOW, R ;

GREENSPOON, N ;

GUO, T ;

ZARZYCKI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8296-8297

[10] Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].

Breslow, R ;

Dong, SD .

CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011

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