ACID CATALYSIS OF EXCITED-STATE DOUBLE-PROTON TRANSFER IN 7-AZAINDOLE

被引：64

作者：

CHANG, CP ^{[1
]}

HWANG, WC ^{[1
]}

KUO, MS ^{[1
]}

CHOU, PT ^{[1
]}

CLEMENTS, JH ^{[1
]}

机构：

[1] UNIV S CAROLINA,DEPT CHEM & BIOCHEM,COLUMBIA,SC 29208

来源：

JOURNAL OF PHYSICAL CHEMISTRY | 1994年 / 98卷 / 35期

关键词：

D O I：

10.1021/j100086a034

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The acid-catalyzed excited-state double-proton transfer (ESDPT) in 7-azaindole has been studied. In carboxylic acids and phosphoric acids, the formation of a 1:1 cyclic hydrogen bonded acid/7-azaindole complex was observed with a remarkably large association constant of >1.0 x 10(4) M(-1). In contrast to alcohol-catalyzed ESDPT, in which the slow ESDPT dynamics involve a large amplitude of solvent reorganization, the rate of acid catalyzed ESDPT is much greater than the decay rate (similar to 1.0 X 10(9) s(-1)) of the normal emission, resulting in a unique tautomer emission. The highly efficient acid-catalyzed ESDPT in 7-azaindole points to the biological application of 7-azaindole as a suitable acid derivative probe in a hydrophobic environment such as in the cell membrane.

引用

页码：8801 / 8805

页数：5

共 24 条

[1] INCORPORATION OF THE AMINO ACID ANALOG TRYPTAZAN INTO THE PROTEIN OF ESCHERICHIA-COLI [J].