ACTIVATION PARAMETERS AND STEREOCHEMISTRY OF AN ANTIBODY-CATALYZED CLAISEN REARRANGEMENT

被引:42
作者
JACKSON, DY [1 ]
LIANG, MN [1 ]
BARTLETT, PA [1 ]
SCHULTZ, PG [1 ]
机构
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 02期
关键词
D O I
10.1002/anie.199201821
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalysis of the same reaction through different mechanisms was attributed to the diversity of the immune response. The chorismate-prephenate conversion 1 --> 3 can be catalyzed by antibodies raised against an analogue of the transition state 2. These antibodies give rise to a variety of activation parameters for the catalysis. An extremely low activation entropy was found for the antibody 11F1-2E11, which supports the notion that conformational restriction may play an important role in antibody catalysis.
引用
收藏
页码:182 / 183
页数:2
相关论文
共 15 条
[1]   TRANSITION-STATE STABILIZATION AND ENZYMIC CATALYSIS - KINETIC AND MOLECULAR-ORBITAL STUDIES OF REARRANGEMENT OF CHORISMATE TO PREPHENATE [J].
ANDREWS, PR ;
SMITH, GD ;
YOUNG, IG .
BIOCHEMISTRY, 1973, 12 (18) :3492-3498
[2]   AN INHIBITOR OF CHORISMATE MUTASE RESEMBLING THE TRANSITION-STATE CONFORMATION [J].
BARTLETT, PA ;
JOHNSON, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7792-7793
[3]   SYNTHESIS AND CLAISEN REARRANGEMENT OF ALKOXYALLYL ENOL ETHERS - EVIDENCE FOR A DIPOLAR TRANSITION-STATE [J].
COATES, RM ;
ROGERS, BD ;
HOBBS, SJ ;
PECK, DR ;
CURRAN, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1160-1170
[4]   THE UNCATALYZED CLAISEN REARRANGEMENT OF CHORISMATE TO PREPHENATE PREFERS A TRANSITION-STATE OF CHAIRLIKE GEOMETRY [J].
COPLEY, SD ;
KNOWLES, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (18) :5306-5308
[5]   ON THE MECHANISM OF REARRANGEMENT OF CHORISMIC ACID AND RELATED-COMPOUNDS [J].
GAJEWSKI, JJ ;
JURAYJ, J ;
KIMBROUGH, DR ;
GANDE, ME ;
GANEM, B ;
CARPENTER, BK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1170-1186
[6]   MECHANISM OF CHORISMATE MUTASE REACTION [J].
GORISCH, H .
BIOCHEMISTRY, 1978, 17 (18) :3700-3705
[7]   ON THE MECHANISM OF THE CHORISMATE MUTASE REACTION [J].
GUILFORD, WJ ;
COPLEY, SD ;
KNOWLES, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) :5013-5019
[8]  
Haslam E., 1974, SHIKIMATE PATHWAY
[9]   CATALYSIS OF CONCERTED REACTIONS BY ANTIBODIES - THE CLAISEN REARRANGEMENT [J].
HILVERT, D ;
CARPENTER, SH ;
NARED, KD ;
AUDITOR, MTM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (14) :4953-4955
[10]   STEREOSPECIFIC CLAISEN REARRANGEMENT CATALYZED BY AN ANTIBODY [J].
HILVERT, D ;
NARED, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) :5593-5594