Heavy atom isotope effects reveal a highly polarized transition state for chorismate mutase

被引:79
作者
Gustin, DJ
Mattei, P
Kast, P
Wiest, O
Lee, L
Cleland, WW
Hilvert, D
机构
[1] Univ Wisconsin, Inst Enzyme Res, Madison, WI 53705 USA
[2] Univ Wisconsin, Dept Biochem, Madison, WI 53705 USA
[3] ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
[4] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
[5] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ja9841759
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:1756 / 1757
页数:2
相关论文
共 29 条
[1]   SECONDARY TRITIUM ISOTOPE EFFECTS AS PROBES OF THE ENZYMIC AND NON-ENZYMIC CONVERSION OF CHORISMATE TO PREPHENATE [J].
ADDADI, L ;
JAFFE, EK ;
KNOWLES, JR .
BIOCHEMISTRY, 1983, 22 (19) :4494-4501
[2]   Synchronous or asynchronous? An ''experimental'' transition state from a direct comparison of experimental and theoretical kinetic isotope effects for a Diels-Alder reaction [J].
Beno, BR ;
Houk, KN ;
Singleton, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) :9984-9985
[3]   CRYSTAL-STRUCTURES OF THE MONOFUNCTIONAL CHORISMATE MUTASE FROM BACILLUS-SUBTILIS AND ITS COMPLEX WITH A TRANSITION-STATE ANALOG [J].
CHOOK, YM ;
KE, HM ;
LIPSCOMB, WN .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (18) :8600-8603
[4]   IDENTIFICATION AND REMOVAL OF IMPEDIMENTS TO BIOCATALYTIC SYNTHESIS OF AROMATICS FROM D-GLUCOSE - RATE-LIMITING ENZYMES IN THE COMMON PATHWAY OF AROMATIC AMINO-ACID BIOSYNTHESIS [J].
DELL, KA ;
FROST, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11581-11589
[5]   Experimental and theoretical kinetic isotope effects for asymmetric dihydroxylation. Evidence supporting a rate-limiting ''(3+2)'' cycloaddition [J].
DelMonte, AJ ;
Haller, J ;
Houk, KN ;
Sharpless, KB ;
Singleton, DA ;
Strassner, T ;
Thomas, AA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) :9907-9908
[6]   ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE [J].
FLEET, GWJ ;
SHING, TKM ;
WARR, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :905-908
[7]   The Claisen rearrangement. Response to solvents and substituents: The case for both hydrophobic and hydrogen bond acceleration in water and for a variable transition state [J].
Gajewski, JJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (05) :219-225
[8]  
Ganem B., 1996, ANGEW CHEM INT EDIT, V35, P936, DOI [DOI 10.1002/ANIE.199609361, 10.1002/anie.199609361, 10.1002/anie.19960936]
[9]   MONOFUNCTIONAL CHORISMATE MUTASE FROM BACILLUS-SUBTILIS - KINETIC AND C-13 NMR-STUDIES ON THE INTERACTIONS OF THE ENZYME WITH ITS LIGANDS [J].
GRAY, JV ;
EREN, D ;
KNOWLES, JR .
BIOCHEMISTRY, 1990, 29 (37) :8872-8878
[10]   MONOFUNCTIONAL CHORISMATE MUTASE FROM BACILLUS-SUBTILIS - FTIR STUDIES AND THE MECHANISM OF ACTION OF THE ENZYME [J].
GRAY, JV ;
KNOWLES, JR .
BIOCHEMISTRY, 1994, 33 (33) :9953-9959