Secondary isotope effects in liquid chromatography behaviour of 2H and 3H labelled solutes and solvents

Valleix, Alain; Carrat, Sandrine; Caussignac, C.; Léonce, Estelle; Tchapla, Alain

doi:10.1016/j.chroma.2006.03.078

Cited by 36 publications

(29 citation statements)

References 48 publications

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“…Generally,a ni ncreasing number of deuterium substitutions increases the potential for chromatographic resolution; having stated this,l abel location, molecule size,m olecule structure,r etention mechanism, retention times,a nd the pH value of the mobile phase may also have an influence. [81] Furthermore,b inding affinities can also be influenced by deuterium isotope effects on van der Waals interactions, which might lead to stabilization or destabilization of the binding to aligand depending on the deuterium position. [75,82] Selective deuteration can also influence the morphology and phase separation kinetics of polymer blends, [83] and alter the thermal, elastic, [84] and optoelectronic properties [85] of conducting polymers.…”

Section: Isotope Effects In Non-covalent Interactionsmentioning

confidence: 99%

Deuterium‐ and Tritium‐Labelled Compounds: Applications in the Life Sciences

Atzrodt¹,

Derdau²,

et al. 2018

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Hydrogen isotopes are unique tools for identifying and understanding biological and chemical processes. Hydrogen isotope labelling allows for the traceless and direct incorporation of an additional mass or radioactive tag into an organic molecule with almost no changes in its chemical structure, physical properties, or biological activity. Using deuterium-labelled isotopologues to study the unique mass-spectrometric patterns generated from mixtures of biologically relevant molecules drastically simplifies analysis. Such methods are now providing unprecedented levels of insight in a wide and continuously growing range of applications in the life sciences and beyond. Tritium ( H), in particular, has seen an increase in utilization, especially in pharmaceutical drug discovery. The efforts and costs associated with the synthesis of labelled compounds are more than compensated for by the enhanced molecular sensitivity during analysis and the high reliability of the data obtained. In this Review, advances in the application of hydrogen isotopes in the life sciences are described.

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Section: Isotope Effects In Non-covalent Interactionsmentioning

confidence: 99%

Deuterium‐ and Tritium‐Labelled Compounds: Applications in the Life Sciences

Atzrodt¹,

Derdau²,

et al. 2018

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“…Previous studies have shown that substitution of protiated LC solvents with deuterated solvents can affect the RT of compounds of interest in some experimental paradigms 23–25 . A shift in RT is observed due to the deuterium isotope effect, which changes the interaction of different compounds with the stationary phase.…”

Section: Resultsmentioning

confidence: 99%

“…The size and direction of any RT shift is dependent on the number of deuterium atoms in a molecule, with compounds with more deuterium atoms showing a larger shift. In most cases, deuterated compounds show less interaction with the stationary phase; in RPLC, they typically elute before the protiated compounds, but there are cases where the reverse has been observed 25 . A large RT shift can affect the data interpretation, especially if it also leads to a change in the retention order of lipids.…”

Section: Resultsmentioning

confidence: 99%

Simple LC-MS Method for Differentiation of Isobaric Phosphatidylserines and Phosphatidylcholines with Deuterated Mobile Phase Additives

et al. 2016

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Lipids from different classes sometimes can exhibit the same exact mass upon electrospray ionization; this presents an analytical challenge in lipidomics. In the negative ionization mode, for example, this can occur with phosphatidylcholines (PCs) and phosphatidylserines (PSs), making them indistinguishable in the absence of fragmentation data. PSs are found at low concentrations in biological samples, making MS/MS spectra difficult to obtain. Moreover, while PCs and PSs are distinguishable in the positive mode, PSs do not ionize as well as PCs, and their ionization is suppressed by the PCs. Here, we show that, in the negative ionization mode, substituting protiated LC-MS additives with their deuterated forms provides a way to distinguish PCs and PSs without chemical derivatization. The method described leverages the differential ionization mechanism of PCs and PSs. PCs are ionized via adduction with salts, whereas PSs ionize via hydrogen abstraction. Substituting the salts used for LC-MS with their deuterated form shifts the mass of PCs by the number of deuterium atoms in the salt, while the mass of PSs remains the same. This comparative shift enables their direct differentiation. We demonstrate that the use of deuterated formate shifts the mass of PCs and provides a direct method to distinguish PCs and PSs, even at biologically-relevant low concentrations. The utility of the method was established and validated in the simultaneous analysis of PCs and PSs in lipid extracts from isolated liver mitochondria in two different rat strains. Thirteen low concentration PSs were identified that would otherwise not have been distinguishable from low concentration PCs.

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“…[81] Auch Bindungsaffinitäten kçnnen Deuteriumisotopeneffekten unterliegen (über die Einwirkung auf (Van-der-Waals-Wechselwirkungen), was,a bhängig von der Deuteriumposition, zu einer Stabilisierung oder Destabilisierung der Bindung an einen Liganden führen kann. [81] Auch Bindungsaffinitäten kçnnen Deuteriumisotopeneffekten unterliegen (über die Einwirkung auf (Van-der-Waals-Wechselwirkungen), was,a bhängig von der Deuteriumposition, zu einer Stabilisierung oder Destabilisierung der Bindung an einen Liganden führen kann.…”

Section: Isotopeneffekte Bei Nicht-kovalenten Wechselwirkungenunclassified

Deuterium‐ und tritiummarkierte Verbindungen: Anwendungen in den modernen Biowissenschaften

Atzrodt¹,

Derdau²,

Kerr

et al. 2018

Angewandte Chemie

108

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Wasserstoffisotope sind einzigartige Werkzeuge zur Identifizierung und Erforschung biologischer oder chemischer Vorgänge. Wasserstoffisotopenmarkierungen erlauben den spurlosen und direkten Einbau einer zusätzlichen Masseneinheit oder eines radioaktiven Markers in ein organisches Molekül, und dies praktisch ohne Änderungen der chemischen Struktur, der physikalischen Eigenschaften oder der biologischen Aktivität. Die Verwendung von deuteriummarkierten Isotopologen zur Untersuchung der spezifischen massenspektrometrischen (MS) Muster, die von Gemischen biologisch relevanter Moleküle hervorgerufen werden, ermöglicht eine drastische Vereinfachung der Analyse. Solche Methoden ermöglichen nun tiefe Einblicke in einen großen, kontinuierlich anwachsenden Bereich von Anwendungen in den Biowissenschaften und darüber hinaus. Speziell Tritium (3H) wird zunehmend eingesetzt, insbesondere in der pharmazeutischen Wirkstoffsuche. Aufwand und Kosten der Synthese markierter Verbindungen werden durch die hohe Empfindlichkeit der Analyse und hohe Zuverlässigkeit der erhaltenen Daten mehr als ausgeglichen. In diesem Aufsatz werden Fortschritte bei der Verwendung von Wasserstoffisotopen in den Biowissenschaften beschrieben.

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Secondary isotope effects in liquid chromatography behaviour of 2H and 3H labelled solutes and solvents

Cited by 36 publications

References 48 publications

Deuterium‐ and Tritium‐Labelled Compounds: Applications in the Life Sciences

Deuterium‐ and Tritium‐Labelled Compounds: Applications in the Life Sciences

Simple LC-MS Method for Differentiation of Isobaric Phosphatidylserines and Phosphatidylcholines with Deuterated Mobile Phase Additives

Deuterium‐ und tritiummarkierte Verbindungen: Anwendungen in den modernen Biowissenschaften

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