Synthesis and silica-based immobilization of monofunctionalized cyclomaltoheptaose derivatives for enantioselective HPLC

被引：30

作者：

Dittmann, H ^{[1
]}

Scharwächter, K ^{[1
]}

König, WA ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

CARBOHYDRATE RESEARCH | 2000年 / 324卷 / 02期

关键词：

monofunctionalized cyclomaltoheptaose (beta-cyclodextrin) derivatives; migration of TBDMS group; immobilized chiral stationary phases; enantioselective HPLC;

D O I：

10.1016/S0008-6215(99)00280-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)cyclomaltoheptaose (6-TBDMS-2,3-Me-beta-CD) and heptakis(2,3,6-tri-O-methyl)cyclomaltoheptaose (per-Me-beta-CD) were monofunctionalized by introduction of a 5-cyanopentyl group attached to one of the O-2, O-3 or O-6 positions and subsequent reduction with lithium aluminum hydride to give the corresponding mono-O-(omega-aminohexyl) derivatives. Alternatively, after attachment of a 7-octenyl group and further epoxidation the corresponding mono-omega-epoxyoctyl derivatives of 6-TBDMS-2,3-Me-beta-CD were obtained. The mono-O-(omega-aminohexyl) derivatives were immobilized by reaction with glycidoxypropyl and 'aldehyde' silica, whereas aminopropyl silica was used for the immobilization of the monoepoxyoctyl derivatives. The immobilized cyclodextrin derivatives were partially evaluated as chiral stationary phases in high-performance liquid chromatography (HPLC) and micro-HPLC. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：75 / 96

页数：22

共 75 条

[1] Synthesis and photoisomerization of an azobenzene derivative bearing two β-cyclodextrin units at both ends [J].

Aoyagi, T ;

Ueno, A ;

Fukushima, M ;

Osa, T .

MACROMOLECULAR RAPID COMMUNICATIONS, 1998, 19 (02) :103-105

[2] CYCLODEXTRIN BONDED PHASES FOR THE LIQUID-CHROMATOGRAPHIC SEPARATION OF OPTICAL, GEOMETRICAL, AND STRUCTURAL ISOMERS [J].

ARMSTRONG, DW ;

DEMOND, W .

JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1984, 22 (09) :411-415

[3] (R)-NAPHTHYLETHYLCARBAMATE-SUBSTITUTED AND (S)-NAPHTHYLETHYLCARBAMATE-SUBSTITUTED BETA-CYCLO-DEXTRIN BONDED STATIONARY PHASES FOR THE REVERSED-PHASE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS [J].

ARMSTRONG, DW ;

CHANG, CD ;

LEE, SH .

JOURNAL OF CHROMATOGRAPHY, 1991, 539 (01) :83-90

[4] Quantitative determination of native and methylated cyclodextrins by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry [J].

Bartsch, H ;

Konig, WA ;

Strassner, M ;

Hintze, U .

CARBOHYDRATE RESEARCH, 1996, 286 :41-53

[5]

BJORNDAL H, 1970, ANGEW CHEM, V82, P643

[6] ARTIFICIAL ENZYMES [J].

BRESLOW, R .

SCIENCE, 1982, 218 (4572) :532-537

[7] CLEAVAGE OF PHOSPHATE-ESTERS BY A CYCLODEXTRIN DIMER CATALYST THAT BINDS THE SUBSTRATES TOGETHER WITH LA3+ AND HYDROGEN-PEROXIDE [J].

BRESLOW, R ;

ZHANG, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7893-7894

[8] MOLECULAR RECOGNITION BY CYCLODEXTRIN DIMERS [J].

BRESLOW, R ;

HALFON, S ;

ZHANG, BL .

TETRAHEDRON, 1995, 51 (02) :377-388

[9] BIOMIMETIC CHEMISTRY [J].

BRESLOW, R .

PURE AND APPLIED CHEMISTRY, 1994, 66 (08) :1573-1582

[10] BIOMIMETIC CHEMISTRY AND ARTIFICIAL ENZYMES - CATALYSIS BY DESIGN [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :146-153

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