Chiral recognition in gas-phase cyclodextrin: Amino acid complexes - Is the three point interaction still valid in the gas phase?

被引：87

作者：

Ahn, S ^{[1
]}

Ramirez, J ^{[1
]}

Grigorean, G ^{[1
]}

Lebrilla, CB ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY | 2001年 / 12卷 / 03期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S1044-0305(00)00220-8

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The validity of the "three-point interaction" model is examined in the guest exchange reaction involving complexes of cyclodextrins and amino acids. The amino acid guest is exchanged in the gas phase in the presence of a gaseous alkyl amine. The net reaction is proton transfer between the protonated amino acid and the alkyl amine. The amino acid is lost as a neutral species. This reaction is sensitive to the chirality of the amino acid. Several amino acids are examined as well as the respective methyl esters to determine the role of the three interacting groups (ammonium, carboxylic acid, and sidechain) in enantioselectivity We find that the three-point interaction model is indeed valid in the gas phase. Enantioselectivity is optimal when two points of attraction and one repulsion is present in the gas-phase complex. The results are supported by molecular modeling calculations. A mechanism for the exchange is proposed. (C) 2001 American Society for Mass Spectrometry.

引用

页码：278 / 287

页数：10

共 39 条

[1]

Booth TD, 1997, CHIRALITY, V9, P96

[2] Chiral recognition is observed in the deprotonation reaction of cytochrome c by (2R)- and (2S)-2-butylamine [J].