Methods for Screening Enantioselective Interactions in the Solution Phase Using ESI‐MS

Schug, Kevin A.

doi:10.1002/9781118180730.ch9

Cited by 2 publications

(1 citation statement)

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“…Different MS‐ionization techniques were used for host–guest chiral recognition investigations. These include: CI (Fales & Wright, ; Winkler, Stahl, & Maquin, ), fast atom bombardment (FAB) (Sawada et al, ; Pócsfalvi et al, ; Sawada, ; Shizuma et al, ), ESI (Sawada et al, ; Schug, ), and matrix‐assisted laser desorption ionization (MALDI) (So, Wan, & Dominic Chan, ). In 1998, Masami Sawada et al have compared between FAB‐MS and laboratory‐made ESI‐MS methods for detecting and quantifying host–guest chiral recognition of different amino acids, and they showed that FAB‐MS was superior to ESI‐MS with respect of chiral recognition sensitivity (Sawada et al, ).…”

Section: Mass Spectrometric Chiral Recognition Mechanismsmentioning

confidence: 99%

Enantioselectivity of mass spectrometry: Challenges and promises

Awad

El‐Aneed

2013

Mass Spec Rev

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With the fast growing market of pure enantiomer drugs and bioactive molecules, new chiral-selective analytical tools have been instigated including the use of mass spectrometry (MS). Even though MS is one of the best analytical tools that has efficiently been used in several pharmaceutical and biological applications, traditionally MS is considered as a "chiral-blind" technique. This limitation is due to the MS inability to differentiate between two enantiomers of a chiral molecule based merely on their masses. Several approaches have been explored to assess the potential role of MS in chiral analysis. The first approach depends on the use of MS-hyphenated techniques utilizing fast and sensitive chiral separation tools such as liquid chromatography (LC), gas chromatography (GC), and capillary electrophoresis (CE) coupled to MS detector. More recently, several alternative separation techniques have been evaluated such as supercritical fluid chromatography (SFC) and capillary electrochromatography (CEC); the latter being a hybrid technique that combines the efficiency of CE with the selectivity of LC. The second approach is based on using the MS instrument solely for the chiral recognition. This method depends on the behavioral differences between enantiomers towards a foreign molecule and the ability of MS to monitor such differences. These behavioral differences can be divided into three types: (i) differences in the enantiomeric affinity for association with the chiral selector, (ii) differences of the enantiomeric exchange rate with a foreign reagent, and (iii) differences in the complex MS dissociation behaviors of the enantiomers. Most recently, ion mobility spectrometry was introduced to qualitatively and quantitatively evaluate chiral compounds. This article provides an overview of MS role in chiral analysis by discussing MS based methodologies and presenting the challenges and promises associated with each approach.

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