A versatile probe for chemoselective capture and analysis of carbonyl compounds in exhaled breath

Knipp, Ralph J.; Li, Mingxiao; Fu, Xiao An; Nantz, Michael H.

doi:10.1039/c5ay01576f

Cited by 12 publications

(19 citation statements)

References 24 publications

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“…4-(2-Aminooxyethyl)-morpholin-4-ium chloride (AMAH) was synthesized according to a published procedure. 30 A popular first-generation e-cigarette blu with a fixed battery output voltage of 3.7 V along with four cartridges (coil resistance 3.0 Ω) was purchased online from Amazon. A newer-generation e-cigarette device consisting of an atomizer EVOD2 made by KangerTech (coil resistance 1.5 Ω) and an iTaste VV V3.0 battery with a digital voltage output of 3.3–5 V was purchased from a local e-cigarette store.…”

Section: Methodsmentioning

confidence: 99%

“…The microreactors have been used for trapping carbonyl compounds in environmental air and exhaled breath. 29,30 Detailed fabrication and characterization procedures of the microreactors for the capture of carbonyl compounds were published elsewhere. 29,30 Each microreactor contains thousands of micropillars.…”

Section: Methodsmentioning

confidence: 99%

“…29,30 Detailed fabrication and characterization procedures of the microreactors for the capture of carbonyl compounds were published elsewhere. 29,30 Each microreactor contains thousands of micropillars. The surface of the micropillars was functionalized with AMAH by infusing a solution of AMAH (32 μL, 1 × 10 –6 mol) in methanol into a microreactor followed by evaporation of the solvent in a vacuum oven.…”

Section: Methodsmentioning

confidence: 99%

“…PVP (5 mg) was added to the eluted solutions to neutralize the positively charged AMAH adducts to AMA (4-(2-aminooxyethyl)morpholine) adducts (Scheme 1). 30 The suspensions were vortex-mixed for 30 s and allowed to stand for 30 min for the sedimentation of PVP particles, after which a 2 μL aliquot was used for GC–MS analysis.…”

Section: Methodsmentioning

confidence: 99%

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Aldehyde Detection in Electronic Cigarette Aerosols

et al. 2017

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Acetaldehyde, acrolein, and formaldehyde are the principal toxic aldehydes present in cigarette smoke and contribute to the risk of cardiovascular disease and noncancerous pulmonary disease. The rapid growth of the use of electronic cigarettes (e-cigarettes) has raised concerns over emissions of these harmful aldehydes. This work determines emissions of these aldehydes in both free and bound (aldehyde–hemiacetal) forms and other carbonyls from the use of e-cigarettes. A novel silicon microreactor with a coating phase of 4-(2-aminooxyethyl)-morpholin-4-ium chloride (AMAH) was used to trap carbonyl compounds in the aerosols of e-cigarettes via oximation reactions. AMAH–aldehyde adducts were measured using gas chromatography–mass spectrometry. 1H nuclear magnetic resonance spectroscopy was used to analyze hemiacetals in the aerosols. These aldehydes were detected in the aerosols of all e-cigarettes. Newer-generation e-cigarette devices generated more aldehydes than the first-generation e-cigarettes because of higher battery power output. Formaldehyde–hemiacetal was detected in the aerosols generated from some e-liquids using the newer e-cigarette devices at a battery power output of 11.7 W and above. The emission of these aldehydes from all e-cigarettes, especially higher levels of aldehydes from the newer-generation e-cigarette devices, indicates the risk of using e-cigarettes.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Aldehyde Detection in Electronic Cigarette Aerosols

et al. 2017

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“…The chemoselectivity of the oximation reaction has stimulated efforts to exploit oxime ether formation not only as a straightforward, efficient coupling approach, but also as a means for identification and quantification of carbonyls in complex mixtures. For example, aminooxy derivatization reagents have been used to selectively tag and/or sequester carbonyl substrates in biological extracts, environmental air and water, exhaled breath, and even living organisms …”

Section: Introductionmentioning

confidence: 99%

Tunable Aminooxy‐Functionalized Monolayer‐Protected Gold Clusters for Nonpolar and Aqueous Oximation Reactions

Sibakoti

Stinger

Adhihetty

et al. 2019

Part & Part Syst Charact

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Aminooxy (–ONH2) groups are well known for their chemoselective reactions with carbonyl compounds, specifically aldehydes and ketones. The versatility of aminooxy chemistry has proven to be an attractive feature that continues to stimulate new applications. This work describes application of aminooxy click chemistry on the surface of gold nanoparticles. A trifunctional amine‐containing aminooxy alkane thiol ligand for use in the functionalization of gold monolayer‐protected clusters (Au MPCs) is presented. Diethanolamine is readily transformed into an organic‐soluble aminooxy thiol (AOT) ligand using a short synthetic path. The synthesized AOT ligand is coated on ≤2‐nm‐diameter hexanethiolate‐(C6S)‐capped Au MPCs using a ligand‐exchange protocol to afford organic‐soluble AOT/C6S (1:1 ratio) Au mixed monolayer‐protected clusters (MMPCs). The synthesis of these Au(C6S)(AOT) MMPCs and representative oximation reactions with various types of aldehyde‐containing molecules is described, highlighting the ease and versatility of the chemistry and how amine protonation can be used to switch solubility characteristics.

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The Influence of β‐Ammonium Substitution on the Reaction Kinetics of Aminooxy Condensations with Aldehydes and Ketones

et al. 2019

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The click‐chemistry capture of volatile aldehydes and ketones by ammonium aminooxy compounds has proven to be an efficient means of analyzing the carbonyl subset in complex mixtures, such as exhaled breath or environmental air. In this work, we examine the carbonyl condensation reaction kinetics of three aminooxy compounds with varying β‐ammonium ion substitution using Fourier transform ion cyclotron resonance mass spectrometry (FT‐ICR‐MS). We determined the activation energies for the reactions of the aminooxy compounds ATM, ADMH and AMAH with a panel of ketones and aldehydes that included acrolein and crotonaldehyde. The measurements indicate that the activation energies for the oximation reactions are quite low, less than 75 kJ mol−1. ADMH is observed to react the fastest with the carbonyls studied. We postulate this result may be attributed to the ADMH ammonium proton effecting a Brønsted‐Lowry acid‐catalyzed elimination of water during the rate‐determining step of oxime ether formation. A theoretical study of oxime ether formation is presented to explain the enhanced reactivity of ADMH relative to the tetraalkylammonium analog ATM.

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A versatile probe for chemoselective capture and analysis of carbonyl compounds in exhaled breath

Abstract: We describe an aminooxy reagent for the capture of trace aldehyde and ketone volatile organic compounds (VOCs) in exhaled breath.

Cited by 12 publications

References 24 publications

Aldehyde Detection in Electronic Cigarette Aerosols

Aldehyde Detection in Electronic Cigarette Aerosols

Tunable Aminooxy‐Functionalized Monolayer‐Protected Gold Clusters for Nonpolar and Aqueous Oximation Reactions

The Influence of β‐Ammonium Substitution on the Reaction Kinetics of Aminooxy Condensations with Aldehydes and Ketones

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