EN-ROUTE TO SYNTHETIC PHOSPHODIESTERASES - SUPRAMOLECULAR PHOSPHORYL-TRANSFER MEDIATED BY AMIDINIUM PHOSPHATE CONTACT ION-PAIRS

被引：74

作者：

GOBEL, MW

BATS, JW

DURNER, G

机构：

[1] Institut für Organische Chemie der Universität, Frankfurt, D-W-6000, Niederurseler Hang

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 02期

关键词：

D O I：

10.1002/anie.199202071

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Proximity effects and electrophilic activation combined account for the accelerated ring-opening in the transesterification of 1 with amidinium alcohol 2. The spatial proximity effects arise in a contact ion-pair of 1 and 2. Electrophilic activation causes the 9000-fold rate enhancement of the reaction of 1 with 2 relative to the reaction with phenylalcohol; the addition of 2 to the transesterification of 1 with phenyl alcohol to form 3 caused a 25-fold rate increase.

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页码：207 / 209

页数：3

相关论文

共 21 条

[1]

AQVIST J, 1989, BIOCHEMISTRY-US, V28, P4680

[2] CATALYSIS BY IMIDAZOLIUM ION AND METAL-IONS IN REACTION OF A PHOSPHATE DIESTER [J].

ATWOOD, L ;

HAAKE, P .

BIOORGANIC CHEMISTRY, 1976, 5 (04) :373-382

[3] BASIC POLYPEPTIDES ACCELERATE THE HYDROLYSIS OF RIBONUCLEIC-ACIDS [J].

BARBIER, B ;

BRACK, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6880-6882

[4] METAL-ACTIVATED HYDROLYTIC CLEAVAGE OF DNA [J].

BASILE, LA ;

RAPHAEL, AL ;

BARTON, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7550-7551

[5] RIBONUCLEASE MIMICS [J].

BRESLOW, R ;

ANSLYN, E ;

HUANG, DL .

TETRAHEDRON, 1991, 47 (14-15) :2365-2376

[6] ARGININE-MEDIATED RNA RECOGNITION - THE ARGININE FORK [J].

CALNAN, BJ ;

TIDOR, B ;

BIANCALANA, S ;

HUDSON, D ;

FRANKEL, AD .

SCIENCE, 1991, 252 (5009) :1167-1171

[7] DEVELOPING ARTIFICIAL HYDROLYTIC METALLOENZYMES BY A UNIFIED MECHANISTIC APPROACH [J].

CHIN, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (05) :145-152

[8] STRUCTURE OF METHYLGUANIDINIUM DIHYDROGENORTHOPHOSPHATE - MODEL COMPOUND FOR ARGININE-PHOSPHATE HYDROGEN-BONDING [J].

COTTON, FA ;

DAY, VW ;

HAZEN, EE ;

LARSEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :4834-4840

[9] STAPHYLOCOCCAL NUCLEASE - PROPOSED MECHANISM OF ACTION BASED ON STRUCTURE OF ENZYME-THYMIDINE 3',5'-BISPHOSPHATE-CALCIUM ION COMPLEX AT 1.5-A RESOLUTION [J].

COTTON, FA ;

HAZEN, EE ;

LEGG, MJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (06) :2551-2555

[10] MECHANISM OF PHOSPHODIESTER CLEAVAGE WITH BETA-CYCLODEXTRIN [J].

HENGGE, AC ;

CLELAND, WW .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1972-1974