TRANSITION-STATE STABILIZATION AND MOLECULAR RECOGNITION - ACCELERATION OF PHOSPHORYL-TRANSFER REACTIONS BY AN ARTIFICIAL RECEPTOR

被引:62
作者
TECILLA, P [1 ]
CHANG, SK [1 ]
HAMILTON, AD [1 ]
机构
[1] UNIV PITTSBURGH, DEPT CHEM, PITTSBURGH, PA 15260 USA
关键词
D O I
10.1021/ja00182a017
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An artificial receptor that is complementary to the proposed trigonal-bipyramidal intermediate for phosphoryl-transfer reactions has been designed. Kinetic measurements with P-31 NMR methods show that the receptor causes up to a 10-fold accleration in the aminolysis of phosphorodiamidic chloride derivatives, proceeding via an associative mechanism.
引用
收藏
页码:9586 / 9590
页数:5
相关论文
共 23 条
[1]  
[Anonymous], 1946, CHEM ENG NEWS, DOI DOI 10.1021/CEN-V024N010.P1375
[2]  
[Anonymous], 1978, TRANSITION STATES BI
[3]  
BOGER J, 1978, CIBA F S, V60, P225
[4]   CONVERSION OF CHOLESTANOL TO 12-KETOCHOLESTANOL AND TO DELTA14-CHOLESTENOL AND DELTA8(14)-CHOLESTENOL BY REMOTE OXIDATION [J].
BRESLOW, R ;
BALDWIN, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :732-&
[5]  
CHANG SJ, UNPUB
[6]   MOLECULAR RECOGNITION OF BIOLOGICALLY INTERESTING SUBSTRATES - SYNTHESIS OF AN ARTIFICIAL RECEPTOR FOR BARBITURATES EMPLOYING 6 HYDROGEN-BONDS [J].
CHANG, SK ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1318-1319
[7]   MOLECULAR RECOGNITION IN AQUEOUS-MEDIA - CONFORMATIONALLY RESTRICTED WATER-SOLUBLE CYCLOPHANES DERIVED FROM 6H,12H-5,11-METHANODIBENZO[B,F][1,5]DIAZOCINE [J].
COWART, MD ;
SUCHOLEIKI, I ;
BUKOWNIK, RR ;
WILCOX, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6204-6210
[8]  
FERSHT A, 1985, ENZYME STRUCTURE MEC, P236
[9]   ASSOCIATIVE AND DISSOCIATIVE MECHANISMS FOR THE REACTIONS OF N-TERT-BUTYL-P-PHENYLPHOSPHONAMIDIC CHLORIDE WITH ISOPROPYLAMINE AND TERT-BUTYLAMINE - COMPETITIVE, KINETIC, AND STEREOCHEMICAL STUDIES [J].
FREEMAN, S ;
HARGER, MJP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (01) :81-90