ON THE TRANSITION-STATE OF THE CHORISMATE-PREPHENATE REARRANGEMENT

被引:48
作者
WIEST, O [1 ]
HOUK, KN [1 ]
机构
[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024
关键词
D O I
10.1021/jo00104a008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ground state and transition structures of the Claisen rearrangement of chorismic acid and chorismate have been calculated using ab initio theory.
引用
收藏
页码:7582 / 7584
页数:3
相关论文
共 42 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]   THE MOLECULAR-CONFORMATION OF CHORISMIC ACID IN THE CRYSTALLINE STATE [J].
AFSHAR, C ;
JAFFE, EK ;
CARRELL, HL ;
MARKHAM, GD ;
RAJAGOPALAN, JS ;
ROSSI, M ;
GLUSKER, JP .
BIOORGANIC CHEMISTRY, 1992, 20 (04) :323-333
[3]   MOLECULAR-ORBITAL STUDIES OF ENZYME CATALYZED REACTIONS - REARRANGEMENT OF CHORISMATE TO PREPHENATE [J].
ANDREWS, PR ;
HADDON, RC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (09) :1921-1929
[4]   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
[5]  
[Anonymous], 1993, SHIKIMIC ACID METABO
[6]  
[Anonymous], 1946, CHEM ENG NEWS, DOI DOI 10.1021/CEN-V024N010.P1375
[7]   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
[8]   BINDING OF A HIGH-ENERGY SUBSTRATE CONFORMER IN ANTIBODY CATALYSIS [J].
CAMPBELL, AP ;
TARASOW, TM ;
MASSEFSKI, W ;
WRIGHT, PE ;
HILVERT, D .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (18) :8663-8667
[9]   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
[10]   THE MONOFUNCTIONAL CHORISMATE MUTASE FROM BACILLUS-SUBTILIS - STRUCTURE DETERMINATION OF CHORISMATE MUTASE AND ITS COMPLEXES WITH A TRANSITION-STATE ANALOG AND PREPHENATE, AND IMPLICATIONS FOR THE MECHANISM OF THE ENZYMATIC-REACTION [J].
CHOOK, YM ;
GRAY, JV ;
KE, HM ;
LIPSCOMB, WN .
JOURNAL OF MOLECULAR BIOLOGY, 1994, 240 (05) :476-500