Imidazolyl cyclodextrins: Artificial serine proteases enabling regiospecific reactions

被引：25

作者：

Yuan, De-Qi ^{[1
]}

Kitagawa, Yumika ^{[1
]}

Aoyama, Keisuke ^{[1
]}

Douke, Toshihiko ^{[1
]}

Fukudome, Makoto ^{[1
]}

Fujita, Kahee ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Dept Mol Med Sci, Nagasaki, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 26期

关键词：

biomimetic synthesis; cyclodextrins; host-guest systems; mass spectrometry; selectivity;

D O I：

10.1002/anie.200701156

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Remote control: The imidazolyl group in a series of imidazolyl cyclodextrins guides the sulfonylation of a specific hydroxy group in the presence of many others to effect a regioselective 1,22 remote functionalization (see structure; Mess = mesitylenesulfonyl, n = 0-2). This process enables the establishment of a novel efficient strategy for the hetero-bifunctionalization and -trifunctionalization of cyclodextrins. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5024 / 5027

页数：4

共 42 条

[1]

[Anonymous], 2004, ANGEW CHEM, V43, P6731, DOI DOI 10.1002/ANGE.200460102

[2] STRUCTURE AND MECHANISM OF CHYMOTRYPSIN [J].

BLOW, DM .

ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (04) :145-152

[3]

BRELOW R, 1991, COMP ORGANIC SYNTHES, V7, P39

[4] ARTIFICIAL ENZYMES [J].

BRESLOW, R .

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

[5] OPTIMIZATION OF METALLOCENE SUBSTRATES FOR BETA-CYCLODEXTRIN REACTIONS [J].

BRESLOW, R ;

TRAINOR, G ;

UENO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2739-2744

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

Breslow, R ;

Dong, SD .

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

[7] Biomimetic hydroxylation of saturated carbons with artificial cytochrome P-450 enzymes - liberating chemistry from the tyranny of functional groups [J].

Breslow, R ;

Yang, J ;

Yan, JM .

TETRAHEDRON, 2002, 58 (04) :653-659

[8] THE COPPER(II) COMPLEX WITH THE IMIDAZOLE-BOUND HISTAMINE DERIVATIVE OF BETA-CYCLODEXTRIN AS A POWERFUL CHIRAL DISCRIMINATING AGENT [J].

CUCINOTTA, V ;

DALESSANDRO, F ;

IMPELLIZZERI, G ;

VECCHIO, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (23) :1743-1745

[9] Bifunctional cyclodextrin metalloenzyme mimics [J].

Dong, SD ;

Breslow, R .

TETRAHEDRON LETTERS, 1998, 39 (51) :9343-9346

[10] Aryl thiol substrate 3-carboxy-4-nitrobenzenethiol strongly stimulating thiol peroxidase activity of glutathione peroxidase mimic 2, 2′-ditellurobis(2-deoxy-β-cyclodextrin) [J].

Dong, ZY ;

Liu, JQ ;

Mao, SZ ;

Huang, X ;

Yang, B ;

Ren, XJ ;

Luo, GM ;

Shen, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (50) :16395-16404

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