Differentiation and quantification of synthetic phosphatidylethanol (PEth) homologues by (1)H- and (13)C-NMR in polar organic solvents.
Wensbo Posaric, David LU
; Andersson, Anders S
LU
; Bergquist, Karl-Erik
and Isaksson, Anders
LU
(2014)
In Analytical and Bioanalytical Chemistry
406(19).
p.4735-4744
- Abstract
- Various phosphatidylethanol (PEth) derivatives, the corresponding reversed positional isomers (RPI-PEths), lyso-PEth-16:0, and penta-deuterium-labeled PEth analogs (d5-PEths), were synthesized by enzyme-independent synthetic routes. A general solvent system consisting of a mixture of acetone-d6 and methanol-d4 (97:3; v/v) was found to provide a good solubilizing capacity and excellent hydrogen-1 NMR ((1)H-NMR) peak resolution of various PEth homologues. Analytical differentiation of PEth from the corresponding RPI-PEth by carbon-13 NMR ((13)C-NMR) was demonstrated by comparison of the (13)C-NMR signals of the carbonyl groups, the allylic positions, and of the β-carbons. An exemplary stable long-term room temperature, DMSO-d6-based, and... (More)
- Various phosphatidylethanol (PEth) derivatives, the corresponding reversed positional isomers (RPI-PEths), lyso-PEth-16:0, and penta-deuterium-labeled PEth analogs (d5-PEths), were synthesized by enzyme-independent synthetic routes. A general solvent system consisting of a mixture of acetone-d6 and methanol-d4 (97:3; v/v) was found to provide a good solubilizing capacity and excellent hydrogen-1 NMR ((1)H-NMR) peak resolution of various PEth homologues. Analytical differentiation of PEth from the corresponding RPI-PEth by carbon-13 NMR ((13)C-NMR) was demonstrated by comparison of the (13)C-NMR signals of the carbonyl groups, the allylic positions, and of the β-carbons. An exemplary stable long-term room temperature, DMSO-d6-based, and proton-sensitive quantitative nuclear magnetic resonance ((1)H-qNMR) independently quantified calibrator comprising PEth-16:0/18:1 for liquid chromatography (tandem) mass spectrometry (LC-MS/MS) analytical applications were prepared by employment of sodium dodecyl sulfate (SDS) as a solubilizing additive. In summary, novel hypothetically occurring PEth derivatives, e.g., RPI-PEths, have been independently synthesized with regio- and stereochemical control. Use of polar organic solvents, e.g., mixtures of acetone-d6 and methanol-d4 or DMSO-d6, improves spectral line shapes as compared to traditional hydrophobic solvents and allow for analytical differentiation between closely related PEth derivatives, as well as LC-MS/MS-independent concentration determination of dissolved single species by employment of (1)H-qNMR. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4452462
- author
- Wensbo Posaric, David
LU
; Andersson, Anders S
LU
; Bergquist, Karl-Erik
and Isaksson, Anders
LU
- organization
- publishing date
- 2014
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Analytical and Bioanalytical Chemistry
- volume
- 406
- issue
- 19
- pages
- 4735 - 4744
- publisher
- Springer
- external identifiers
-
- pmid:24866709
- wos:000339155500017
- scopus:84904499295
- pmid:24866709
- ISSN
- 1618-2642
- DOI
- 10.1007/s00216-014-7826-4
- language
- English
- LU publication?
- yes
- id
- a70dc689-0395-436c-8ce7-832192f96f3c (old id 4452462)
- alternative location
- http://www.ncbi.nlm.nih.gov/pubmed/24866709?dopt=Abstract
- date added to LUP
- 2016-04-01 10:16:24
- date last changed
- 2022-01-25 21:33:49
@article{a70dc689-0395-436c-8ce7-832192f96f3c,
abstract = {{Various phosphatidylethanol (PEth) derivatives, the corresponding reversed positional isomers (RPI-PEths), lyso-PEth-16:0, and penta-deuterium-labeled PEth analogs (d5-PEths), were synthesized by enzyme-independent synthetic routes. A general solvent system consisting of a mixture of acetone-d6 and methanol-d4 (97:3; v/v) was found to provide a good solubilizing capacity and excellent hydrogen-1 NMR ((1)H-NMR) peak resolution of various PEth homologues. Analytical differentiation of PEth from the corresponding RPI-PEth by carbon-13 NMR ((13)C-NMR) was demonstrated by comparison of the (13)C-NMR signals of the carbonyl groups, the allylic positions, and of the β-carbons. An exemplary stable long-term room temperature, DMSO-d6-based, and proton-sensitive quantitative nuclear magnetic resonance ((1)H-qNMR) independently quantified calibrator comprising PEth-16:0/18:1 for liquid chromatography (tandem) mass spectrometry (LC-MS/MS) analytical applications were prepared by employment of sodium dodecyl sulfate (SDS) as a solubilizing additive. In summary, novel hypothetically occurring PEth derivatives, e.g., RPI-PEths, have been independently synthesized with regio- and stereochemical control. Use of polar organic solvents, e.g., mixtures of acetone-d6 and methanol-d4 or DMSO-d6, improves spectral line shapes as compared to traditional hydrophobic solvents and allow for analytical differentiation between closely related PEth derivatives, as well as LC-MS/MS-independent concentration determination of dissolved single species by employment of (1)H-qNMR.}},
author = {{Wensbo Posaric, David and Andersson, Anders S and Bergquist, Karl-Erik and Isaksson, Anders}},
issn = {{1618-2642}},
language = {{eng}},
number = {{19}},
pages = {{4735--4744}},
publisher = {{Springer}},
series = {{Analytical and Bioanalytical Chemistry}},
title = {{Differentiation and quantification of synthetic phosphatidylethanol (PEth) homologues by (1)H- and (13)C-NMR in polar organic solvents.}},
url = {{https://lup.lub.lu.se/search/files/1703695/5049390.pdf}},
doi = {{10.1007/s00216-014-7826-4}},
volume = {{406}},
year = {{2014}},
}