A comparison of NH-π versus lone pair hydrogen bonding effects on carbon acid pKa shifts

被引:48
作者
Snowden, TS [1 ]
Bisson, AP [1 ]
Anslyn, EV [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1021/ja991039a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:6324 / 6325
页数:2
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共 22 条
[1]   DO ENZYMES STABILIZE TRANSITION-STATES BY ELECTROSTATIC INTERACTIONS OR PK(A) BALANCE - THE CASE OF TRIOSE PHOSPHATE ISOMERASE (TIM) [J].
ALAGONA, G ;
GHIO, C ;
KOLLMAN, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (39) :9855-9862
[2]   Structure of 4-chlorobenzoyl coenzyme A dehalogenase determined to 1.8 angstrom resolution: An enzyme catalyst generated via adaptive mutation [J].
Benning, MM ;
Taylor, KL ;
Liu, RQ ;
Yang, G ;
Xiang, H ;
Wesenberg, G ;
DunawayMariano, D ;
Holden, HM .
BIOCHEMISTRY, 1996, 35 (25) :8103-8109
[3]   Recognition of anions through NH-pi hydrogen bonds in a bicyclic cyclophane-selectivity for nitrate [J].
Bisson, AP ;
Lynch, VM ;
Monahan, MKC ;
Anslyn, EV .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (21) :2340-2342
[4]  
Dempsey B, 1979, IONIZATION CONSTANTS, V23, P989
[5]   UNDERSTANDING THE RATES OF CERTAIN ENZYME-CATALYZED REACTIONS - PROTON ABSTRACTION FROM CARBON ACIDS, ACYL-TRANSFER REACTIONS, AND DISPLACEMENT-REACTIONS OF PHOSPHODIESTERS [J].
GERLT, JA ;
GASSMAN, PG .
BIOCHEMISTRY, 1993, 32 (45) :11943-11952
[6]   Understanding enzymic catalysis: The importance of short, strong hydrogen bonds [J].
Gerlt, JA ;
Kreevoy, MM ;
Cleland, WW ;
Frey, PA .
CHEMISTRY & BIOLOGY, 1997, 4 (04) :259-267
[7]  
Guthrie JP, 1996, CHEM BIOL, V3, P163
[8]   ELECTROSTATIC STABILIZATION CAN EXPLAIN THE UNEXPECTED ACIDITY OF CARBON ACIDS IN ENZYME-CATALYZED REACTIONS [J].
GUTHRIE, JP ;
KLUGER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11569-11572
[9]  
HIGUCHI T, 1956, ANAL CHEM, V28, P1507
[10]   EQNMR - A COMPUTER-PROGRAM FOR THE CALCULATION OF STABILITY-CONSTANTS FROM NUCLEAR-MAGNETIC-RESONANCE CHEMICAL-SHIFT DATA [J].
HYNES, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (02) :311-312