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Gas-phase chiral separations by ion mobility spectrometry.

Analytical chemistry (2006-12-15)
Prabha Dwivedi, Ching Wu, Laura M Matz, Brian H Clowers, William F Siems, Herbert H Hill
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Butanol, puriss. p.a., reag. Ph. Eur., ≥99.5% (GC)
Sigma-Aldrich
2-Butanol, ReagentPlus®, ≥99%
Supelco
2-Butanol, analytical standard
Sigma-Aldrich
2-Butanol, anhydrous, 99.5%
Sigma-Aldrich
(R)-(−)-2-Butanol, 99%
Sigma-Aldrich
Aluminum-tri-sec-butoxide, 97%
Sigma-Aldrich
Aluminum-tri-sec-butoxide, 99.99% trace metals basis
Sigma-Aldrich
(S)-(+)-2-Butanol, 99%