Gas-phase chiral separations by ion mobility spectrometry

被引:219
作者
Dwivedi, Prabha
Wu, Ching
Matz, Laura M.
Clowers, Brian H.
Siems, William F.
Hill, Herbert H., Jr. [1 ]
机构
[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA
[2] Washington State Univ, Ctr Multiphase Environm Res, Pullman, WA 99164 USA
[3] Excellims Corp, Maynard, MA 01754 USA
关键词
D O I
10.1021/ac0608772
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
This article introduces the concept of chiral ion mobility spectrometry (CIMS) and presents examples demonstrating the gas-phase separation of enantiomers of a wide range of racemates including pharmaceuticals, amino acids, and carbohydrates. CIMS is similar to traditional ion mobility spectrometry, where gas-phase ions, when subjected to a potential gradient, are separated at atmospheric pressure due to differences in their shapes and sizes. In addition to size and shape, CIMS separates ions based on their stereospecific interaction with a chiral gas. In order to achieve chiral discrimination by CIMS, an asymmetric environment was provided by doping the drift gas with a volatile chiral reagent. In this study (S)-(+)-2-butanol was used as a chiral modifier to demonstrate enantiomeric separations of atenolol, serine, methionine, threonine, methyl alpha-glucopyranoside, glucose, penicillamine, valinol, phenylalanine, and tryptophan from their respective racemic mixtures.
引用
收藏
页码:8200 / 8206
页数:7
相关论文
共 53 条
[1]   Chiral recognition in gas-phase cyclodextrin: Amino acid complexes - Is the three point interaction still valid in the gas phase? [J].
Ahn, S ;
Ramirez, J ;
Grigorean, G ;
Lebrilla, CB .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2001, 12 (03) :278-287
[2]   Using different drift cases to change separation factors (α) in ion mobility spectrometry [J].
Asbury, GR ;
Hill, HH .
ANALYTICAL CHEMISTRY, 2000, 72 (03) :580-584
[3]  
Asbury GR, 2000, J MICROCOLUMN SEP, V12, P172, DOI 10.1002/(SICI)1520-667X(2000)12:3<172::AID-MCS7>3.0.CO
[4]  
2-W
[5]   RACEMIZATION REACTION OF ASPARTIC-ACID AND ITS USE IN DATING FOSSIL BONES - (OLDUVAI GORGE 5,000-70,000-YEARS-OLD RANGE HOMINIDS) [J].
BADA, JL ;
PROTSCH, R .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1973, 70 (05) :1331-1334
[6]   Meteoritics - Extraterrestrial handedness? [J].
Bada, JL .
SCIENCE, 1997, 275 (5302) :942-943
[7]   Chiral recognition by proton transfer reactions with optically active amines and alcohols [J].
Bagheri, H ;
Chen, H ;
Cooks, RG .
CHEMICAL COMMUNICATIONS, 2004, (23) :2740-2741
[8]   Post-translational amino acid isomerization - A functionally important D-amino acid in an excitatory peptide [J].
Buczek, O ;
Yoshikami, D ;
Bulaj, G ;
Jimenez, EC ;
Olivera, BM .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (06) :4247-4253
[9]   CHIRAL HOST-GUEST RECOGNITION IN AN ION-MOLECULE REACTION [J].
CHU, IH ;
DEARDEN, DV ;
BRADSHAW, JS ;
HUSZTHY, P ;
IZATT, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4318-4320
[10]  
CLOWERS BH, 2002, 50 ANN AM SOC MASS S