The first chemical synthesis of a cyclodextrin heteroduplex

被引：22

作者：

Bistri, O ^{[1
]}

Lecourt, T ^{[1
]}

Mallet, JM ^{[1
]}

Sollogoub, M ^{[1
]}

Sinay, P ^{[1
]}

机构：

[1] Ecole Normale Super, UMR CNRS 8642, Dept Chim, F-75231 Paris 05, France

来源：

CHEMISTRY & BIODIVERSITY | 2004年 / 1卷 / 01期

关键词：

D O I：

10.1002/cbdv.200490004

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：

The synthesis of the first heteroduplex of cyclodextrin (CD) 11, i.e., a compound in which the two primary rims of alpha- and beta-CDs are doubly connected, was achieved. The selected strategy involved a Sonogashira coupling of propargylated beta-CD 6 and iodo-alkenyl alpha-CD 4 to singly connect the two CDs. A ring-closing metathesis (RCM) of the heterodimer 9 afforded the second bridge, final deprotection and reductions giving acces to 11.

引用

页码：129 / 137

页数：9

共 57 条

[1] New supramolecular assemblies of a cyclodextrin-grafted chitosan through specific complexation [J].

Auzély-Velty, R ;

Rinaudo, M .

MACROMOLECULES, 2002, 35 (21) :7955-7962

[2]

AUZELYVELTY R, UNPUB

[3] Cyclodextrin dimers as cleavable carriers of photodynamic sensitizers [J].

Baugh, SDP ;

Yang, ZW ;

Leung, DK ;

Wilson, DM ;

Breslow, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12488-12494

[4] 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

[5] Sequence selective binding of peptides by artificial receptors in aqueous solution [J].

Breslow, R ;

Yang, ZW ;

Ching, R ;

Trojandt, G ;

Odobel, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) :3536-3537

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

Breslow, R ;

Dong, SD .

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

[7] VERY FAST ESTER HYDROLYSIS BY A CYCLODEXTRIN DIMER WITH A CATALYTIC LINKING GROUP [J].

BRESLOW, R ;

ZHANG, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5882-5883

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

BRESLOW, R .

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

[9] Cholesterol recognition and binding by cyclodextrin dimers [J].

Breslow, R ;

Zhang, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8495-8496

[10] STRONG BINDING OF DITOPIC SUBSTRATES BY A DOUBLY LINKED OCCLUSIVE C1 CLAMSHELL AS DISTINGUISHED FROM AN AVERSIVE C2 LOVESEAT CYCLODEXTRIN [J].

BRESLOW, R ;

CHUNG, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9659-9660

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