Metallocyclodextrin catalysts for hydrolysis of phosphate triesters

被引：38

作者：

Barr, L

Easton, CJ ^{[1
]}

Lee, K

Lincoln, SF

Simpson, JS

机构：

[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

[2] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(02)01757-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper complexes of 6(A)-(2-aminoethylamino)- and 6(A)-(3-aminopropylamino)-6(A)-deoxy-beta-cyclodextrin catalyse the hydrolysis of 4-tert-butyl-2-nitrophenyl dimethyl phosphate, with k(inc) = 3.1x10(-2) and 2.3x10(-2) s(-1), and K-d = 4.3x10(-4) and 1.2x10(-3) M, respectively, in 0.05 M pH 7.0 HEPES buffer at 298 K. This corresponds to rate accelerations of more than 95 000 and 70 000 times for reaction of the cyclodextrin-bound species. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：7797 / 7800

页数：4

相关论文

共 39 条

[1] SYNTHESIS AND TRANSACYLATING ACTIVITY OF ISOMERIC CO(III)-CYCLODEXTRIN ARTIFICIAL METALLOENZYMES [J].

AKKAYA, EU ;

CZARNIK, AW .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1992, 5 (08) :540-548

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

Breslow, R ;

Dong, SD .

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

[3] 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

[4] COMPLEXATION OF PHENYLALANINE AND HISTIDINE BY BETA-CYCLODEXTRIN, 6(A)-(3-AMINOPROPYLAMINO)-6(A)-DEOXY-BETA-CYCLODEXTRIN AND ITS METALLOCYCLODEXTRINS IN AQUEOUS-SOLUTION [J].

BROWN, SE ;

HASKARD, CA ;

EASTON, CJ ;

LINCOLN, SF .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1995, 91 (06) :1013-1018

[5] METALLOCYCLODEXTRINS OF 6(A)-(3-AMINOPROPYLAMINO)-6(A)-DEOXY-BETA-CYCLODEXTRIN - THEIR FORMATION AND ENANTIOSELECTIVE COMPLEXATION OF (R)-TRYPTOPHAN AND (S)-TRYPTOPHAN ANIONS IN AQUEOUS-SOLUTION [J].

BROWN, SE ;

COATES, JH ;

EASTON, CJ ;

LINCOLN, SF .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1994, 90 (05) :739-743

[6] TRYPTOPHAN ANION COMPLEXES OF BETA-CYCLODEXTRIN (CYCLOMALTAHEPTAOSE), AN AMINOPROPYLAMINO-BETA-CYCLODEXTRIN AND ITS ENANTIOSELECTIVE NICKEL(II) COMPLEX [J].

BROWN, SE ;

COATES, JH ;

EASTON, CJ ;

VANEYK, SJ ;

LINCOLN, SF ;

MAY, BL ;

STILE, MA ;

WHALLAND, CB ;

WILLIAMS, ML .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :47-47

[7] THE COORDINATION CHEMISTRY OF DIVALENT COBALT, NICKEL, AND COPPER .13. CHARACTERIZATION AND STABILITY-CONSTANTS OF COPPER(II) SPECIES ISOLATED FROM MIXED-LIGAND SOLUTIONS - CRYSTAL-STRUCTURE OF THE COMPLEX (PYRDINE-2,6-DICARBOXYLATO)(N,N,N',N'-TETRAMETHYL-1,3-DIAMINOPROPANE)COPPER(II) [J].

DUPREEZ, JGH ;

VANBRECHT, BJAM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1989, (02) :253-257

[8]

Easton C.J., 1999, MODIFIED CYCLODEXTRI, P1

[9]

Eto M., 1992, Handbook of Organophosphorus Chemistry, P807

[10]

FURLONG CE, 1998, BIOREMEDIATION, V2, P521

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