Chiral differentiation of some cyclopentane and cyclohexane <i>β</i>-amino acid enantiomers through ion/molecule reactions

Hyyryläinen, Anna R. M.; Pakarinen, Jaana M. H.; Forró, Enikő; Fülöp, Ferenc; Vainiotalo, Pirjo

doi:10.1016/j.jasms.2009.02.018

Cited by 18 publications

(14 citation statements)

References 44 publications

(40 reference statements)

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“…Lebrilla group used cyclodextrin and maltose as the host molecules and affluxed alkylamine as the reaction gas to distinguish chiral amino acid, measuring the difference in the reaction ratio of amino acid with propylamine and ethylenediamine. 11 In 2009, Hyyrylainen group used ion/molecular reaction method in propylamine and triethylamine gas with cyclodextrin and crown ether compounds being the host to distinguish a series of cyclopentane and cyclohexane amino acid of 2 chiral centers, 35 expanding the application of ionic molecular reaction method.…”

Section: Ion/molecule (Equilibrium) Reactionsmentioning

confidence: 99%

Analysis of stereoisomers of chiral drug by mass spectrometry

2018

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Chiral molecules are of great importance in the life science since individual enantiomers may differ in biological activity, mechanism, and toxicity, making it necessary to explore efficient chiral analysis methods. Chromatography approaches are often used to differentiate enantiomers while mass spectrometry (MS) was thought to be blind in chiral analysis. With the development of MS technique, it began to play a more and more crucial part in chiral observation. In this review, we will give a detailed introduction of the analysis methods related to MS for chiral drugs, including its mechanism, applications, and future development.

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Section: Ion/molecule (Equilibrium) Reactionsmentioning

confidence: 99%

Analysis of stereoisomers of chiral drug by mass spectrometry

2018

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“…It is clear that MS possesses advantages such as rapid analysis, high sensitivity, and reduced sample consumption; it also does not necessitate isotope labeling or other derivatization treatment to analytes. Currently, there are 4 major types of MS techniques used in chiral recognition: (1) the host‐guest method, (2) ion/molecule (equilibrium) reactions, (3) collision‐induced dissociation of diastereomeric complex (which includes the kinetic method [KM], the fixed ligand KM, and the chiral recognition ratio method) and (4) ion mobility MS . The most commonly used type is KM because the experimental data interpretation is much easier because only the relative abundances of 2 fragment ions are needed and isomer separation is not necessary.…”

Section: Introductionmentioning

confidence: 99%

Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and Zn^II using mass spectrometry

Wang

Chen

et al. 2018

J Mass Spectrom

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In this study, a mass spectrometry (MS)-based kinetic method (KM) is shown to be successful at analyzing a multichiral center drug stereoisomer, entecavir (ETV), both qualitatively and quantitatively. On the basis of the KM, the bivalent complex ion [M (A)(ref*) ] (M = divalent metal ion, A = analyte, and ref* = chiral reference) was set as precursor ion in MS/MS. The experiment results suggest strong chiral selectivity between ETV and its isomers when using Zn coordinated with the chiral reference R-besivance (R-B). The logarithm of the fragment ion abundance ratio and the enantiomeric percentage (%) exhibits a strong linear relation because of the competitive loss of the reference and analyte. The product ion pair [Zn (R-B)A-H] (m/z 733) and [Zn (R-B) -H] (m/z 849), together with [R-B + H] (m/z 394) and [A + H] (m/z 278), can realize the identification of ETV and all of its chiral isomers. Theoretical calculation were also performed using the B3LYP functional with the 6-31G* and LanL2DZ basis set to clarify the mechanism of structural difference of these bivalent complex ions. The results reveal that MS-KM can be used to detect optical impurities without a chiral chromatographic column and fussy sample pretreatment. The established method has been used to determine stereoisomeric impurities of less than 0.1% in ETV crude drug, a demonstration of its simple and effective nature for rapid detection of stereoisomeric impurities.

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“…The fast and sensitive performance of mass spectrometry (MS) places it among the most promising techniques in drug analysis. However, despite significant success in the development of MS-based chiral recognition methods [7][8][9][10][11][12][13][14][15], many gas-phase processes which lie behind this recognition are still poorly understood.…”

Section: Introductionmentioning

confidence: 99%

High-energy collisions of protonated enantiopure amino acids with a chiral target gas

Kulyk

Rebrov

Stockett

et al. 2015

International Journal of Mass Spectrometry

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Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

Cited by 18 publications

References 44 publications

Analysis of stereoisomers of chiral drug by mass spectrometry

Analysis of stereoisomers of chiral drug by mass spectrometry

Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and Zn^II using mass spectrometry

High-energy collisions of protonated enantiopure amino acids with a chiral target gas

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Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

Cited by 18 publications

References 44 publications

Analysis of stereoisomers of chiral drug by mass spectrometry

Analysis of stereoisomers of chiral drug by mass spectrometry

Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and ZnII using mass spectrometry

High-energy collisions of protonated enantiopure amino acids with a chiral target gas

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Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and Zn^II using mass spectrometry