Conformational flexibility in small biomolecules: tryptamine and 3-indole-propionic acid

被引：42

作者：

Carney, JR ^{[1
]}

Zwier, TS ^{[1
]}

机构：

[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

CHEMICAL PHYSICS LETTERS | 2001年 / 341卷 / 1-2期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0009-2614(01)00464-X

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：

A combined experimental and theoretical study is used to probe the conformational preferences of two flexible tryptophan analogs, tryptamine (TRA) and 3-indole-propionic acid (IPA). Resonant ion-dip infrared spectroscopy provides infrared spectra of single conformations of these molecules free from interference from one another. Density functional theory Becke3LYP calculations are used to predict relative energies for the conformers, while relaxed potential energy scans determine the barrier heights separating the minima. The different forms of the potential energy surfaces along the flexible coordinates for the two molecules provide a coherent explanation for the observed conformational preferences. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

收藏

页码：77 / 85

页数：9

相关论文

共 28 条

[1] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[2] FLUORESCENCE SPECTROSCOPY OF JET-COOLED TRYPTOPHAN PEPTIDES [J].

CABLE, JR ;

TUBERGEN, MJ ;

LEVY, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) :9032-9039

[3] The infrared and ultraviolet spectra of individual conformational isomers of biomolecules: Tryptamine [J].

Carney, JR ;

Zwier, TS .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (38) :8677-8688

[4] OBSERVATION AND DESCRIPTION OF A NEW TYPE OF TRANSIENT IN ROTATIONAL COHERENCE SPECTROSCOPY [J].

CONNELL, LL ;

CORCORAN, TC ;

JOIREMAN, PW ;

FELKER, PM .

JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (04) :1229-1232

[5] CONFORMATIONAL-ANALYSIS OF JET-COOLED TRYPTOPHAN ANALOGS BY ROTATIONAL COHERENCE SPECTROSCOPY [J].

CONNELL, LL ;

CORCORAN, TC ;

JOIREMAN, PW ;

FELKER, PM .

CHEMICAL PHYSICS LETTERS, 1990, 166 (5-6) :510-516

[6] Conformational structures of 3-phenyl-1-propionic acid, its p-hydroxy derivative, and its hydrated clusters [J].

Dickinson, JA ;

Joireman, PW ;

Randall, RW ;

Robertson, EG ;

Simons, JP .

JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (04) :513-521

[7] Conformational choice, hydrogen bonding, and rotation of the S1←S0 electronic transition moment in 2-phenylethyl alcohol, 2-phenylethylamine, and their water clusters [J].

Dickinson, JA ;

Hockridge, MR ;

Kroemer, RT ;

Robertson, EG ;

Simons, JP ;

McCombie, J ;

Walker, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2622-2632

[8] ORIGIN OF METHYL CONFORMATIONAL PREFERENCES AND ROTATIONAL BARRIERS IN THE GROUND-STATES, EXCITED TRIPLET-STATES, RADICAL CATIONS, AND RADICAL-ANIONS OF MOLECULES HAVING CH3-C=X FUNCTIONALITIES [J].

DORIGO, AE ;

PRATT, DW ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6591-6600

[9] GAUSSIAN-BASIS SETS FOR USE IN CORRELATED MOLECULAR CALCULATIONS .1. THE ATOMS BORON THROUGH NEON AND HYDROGEN [J].

DUNNING, TH .

JOURNAL OF CHEMICAL PHYSICS, 1989, 90 (02) :1007-1023

[10] ROTATIONAL COHERENCE SPECTROSCOPY - STUDIES OF THE GEOMETRIES OF LARGE GAS-PHASE SPECIES BY PICOSECOND TIME-DOMAIN METHODS [J].

FELKER, PM .

JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (20) :7844-7857