Bifunctional binding and catalysis

被引:26
作者
Breslow, Ronald [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1080/10610279308040656
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cyclodextrin dimers can show very strong binding of appropriate substrates, and also significant geometric recognition. When the link between the two cyclodextrin rings carries a catalytic group, good turnover catalysis can be observed. The binding and catalytic properties are comparable with those of some catalytic antibodies. When a cyclodextrin binding group carries two catalytic groups, cooperative bifunctional catalysis can be observed. The details of this process are best understood in a mimic of ribonuclease, but other reactions that show bifunctional catalysis by these enzyme mimics are also being explored. The design of these catalysts was strongly influenced by detailed mechanistic studies of bifunctional catalysed cleavage and isomerization of RNA. A brief description of this evidence for the mechanism is presented. Recent findings on the properties of an isomer of DNA are also discussed.
引用
收藏
页码:111 / 118
页数:8
相关论文
共 24 条
[1]   ON THE MECHANISM OF CATALYSIS BY RIBONUCLEASE - CLEAVAGE AND ISOMERIZATION OF THE DINUCLEOTIDE UPU CATALYZED BY IMIDAZOLE BUFFERS [J].
ANSLYN, E ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4473-4482
[2]   PROTON INVENTORY OF A BIFUNCTIONAL RIBONUCLEASE MODEL [J].
ANSLYN, E ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8931-8932
[3]   GEOMETRIC EVIDENCE ON THE RIBONUCLEASE MODEL MECHANISM [J].
ANSLYN, E ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5972-5973
[4]   ON THE MECHANISM OF ACTION OF RIBONUCLEASES - DINUCLEOTIDE CLEAVAGE CATALYZED BY IMIDAZOLE AND ZN-2+ [J].
BRESLOW, R ;
HUANG, DL ;
ANSLYN, E .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (06) :1746-1750
[5]   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
[6]   A NEGATIVE CATALYTIC TERM REQUIRES A COMMON INTERMEDIATE IN THE IMIDAZOLE BUFFER CATALYZED CLEAVAGE AND REARRANGEMENT OF RIBODINUCLEOTIDES [J].
BRESLOW, R ;
HUANG, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9621-9623
[7]   BETA-CYCLODEXTRINYLBISIMIDAZOLE, A MODEL FOR RIBONUCLEASE [J].
BRESLOW, R ;
DOHERTY, JB ;
GUILLOT, G ;
LIPSEY, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (10) :3227-3229
[8]   ARTIFICIAL TRANSAMINASES LINKING PYRIDOXAMINE TO BINDING CAVITIES - CONTROLLING THE GEOMETRY [J].
BRESLOW, R ;
CANARY, JW ;
VARNEY, M ;
WADDELL, ST ;
YANG, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5212-5219
[9]   SEQUENTIAL GENERAL BASE ACID CATALYSIS IN THE HYDROLYSIS OF RNA BY IMIDAZOLE [J].
BRESLOW, R ;
LABELLE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) :2655-2659
[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