The aromatic sidechains of amino acids as neutral donor groups for alkali metal cations

被引:79
作者
Gokel, GW
机构
[1] Washington Univ, Sch Med, Program Chem Biol, St Louis, MO 63110 USA
[2] Washington Univ, Sch Med, Dept Mol Biol, St Louis, MO 63110 USA
[3] Washington Univ, Sch Med, Dept Pharmacol, St Louis, MO 63110 USA
[4] Washington Univ, Sch Med, Dept Chem, St Louis, MO 63110 USA
关键词
D O I
10.1039/b305483g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An aromatic residue that can serve as a pi- donor occurs in all known protein sequences about one out of every 11 amino acids. Benzene, phenol, and indole, the sidechains of phenylalanine, tyrosine, and tryptophan, are particularly important in protein structure. Solid state structures confirm the interactions of these neutral arenes, along with double and triple bonds, with sodium and potassium cations.
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页码:2847 / 2852
页数:6
相关论文
共 43 条
[1]  
ARNOLD KA, 1988, TETRAHEDRON LETT, P3025
[2]   PI GROUPS IN ION-PAIR BONDING - STABILIZATION OF DIANION OF NAPHTHALENE BY LITHIUM TETRAMETHYLETHYLENEDIAMINE [J].
BROOKS, JJ ;
RHINE, W ;
STUCKY, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (21) :7346-&
[3]   AMINO-AROMATIC INTERACTIONS IN PROTEINS [J].
BURLEY, SK ;
PETSKO, GA .
FEBS LETTERS, 1986, 203 (02) :139-143
[4]   Competitive solvation of K+ by benzene and water:: Cation-π interactions and π-hydrogen bonds [J].
Cabarcos, OM ;
Weinheimer, CJ ;
Lisy, JM .
JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (13) :5151-5154
[5]   Solution- and solid-state evidence for alkali metal cation-π interactions with indole, the side chain of tryptophan [J].
De Wall, SL ;
Meadows, ES ;
Barbour, LJ ;
Gokel, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5613-5614
[6]   Cation-π complexation of potassium cation with the phenolic sidechain of tyrosine [J].
De Wall, SL ;
Barbour, LJ ;
Gokel, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (36) :8405-8406
[7]   Synthetic receptors as models for alkali metal cation-π binding sites in proteins [J].
De Wall, SL ;
Meadows, ES ;
Barbour, LJ ;
Gokel, GW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (12) :6271-6276
[8]  
DEAKYNE CA, 1985, J AM CHEM SOC, V107, P474
[9]  
Desiraju G., 2001, WEAK HYDROGEN BOND S
[10]   THE C-H...O HYDROGEN-BOND IN CRYSTALS - WHAT IS IT [J].
DESIRAJU, GR .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :290-296