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Int. J. Mol. Sci. 2016, 17(7), 1024; doi:10.3390/ijms17071024

Fourier Transform Mass Spectrometry and Nuclear Magnetic Resonance Analysis for the Rapid and Accurate Characterization of Hexacosanoylceramide

1
Merck & Co. Inc., Merck Research Laboratories, Dept. of Medicinal Chemistry, West Point, PA 19486, USA
2
DuPont Marshall R & D Laboratories, Philadelphia, PA 19146, USA
Current Address: Lubrizol Advanced Materials, Inc., 9911 Brecksville Rd., Brecksville, OH 44141-3201, USA
Current Address: DuPont Corporate Center for Analytical Sciences, DuPont Experimental Station, 200 Powder Mill Rd., PO Box 8352, Wilmington, DE 19803, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Laszlo Prokai
Received: 29 February 2016 / Revised: 3 May 2016 / Accepted: 16 May 2016 / Published: 28 June 2016
(This article belongs to the Special Issue Fourier Transform Mass Spectrometry in Molecular Sciences)
View Full-Text   |   Download PDF [1744 KB, uploaded 28 June 2016]   |  

Abstract

Ceramides are a central unit of all sphingolipids which have been identified as sites of biological recognition on cellular membranes mediating cell growth and differentiation. Several glycosphingolipids have been isolated, displaying immunomodulatory and anti-tumor activities. These molecules have generated considerable interest as potential vaccine adjuvants in humans. Accurate analyses of these and related sphingosine analogues are important for the characterization of structure, biological function, and metabolism. We report the complementary use of direct laser desorption ionization (DLDI), sheath flow electrospray ionization (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FTICR MS) and high-field nuclear magnetic resonance (NMR) analysis for the rapid, accurate identification of hexacosanoylceramide and starting materials. DLDI does not require stringent sample preparation and yields representative ions. Sheath-flow ESI yields ions of the product and byproducts and was significantly better than monospray ESI due to improved compound solubility. Negative ion sheath flow ESI provided data of starting materials and products all in one acquisition as hexacosanoic acid does not ionize efficiently when ceramides are present. NMR provided characterization of these lipid molecules complementing the results obtained from MS analyses. NMR data was able to differentiate straight chain versus branched chain alkyl groups not easily obtained from mass spectrometry. View Full-Text
Keywords: ceramides; sphingolipids; adjuvants; Fourier transform ion cyclotron resonance mass spectrometry (FTICR MS); nuclear magnetic resonance (NMR); direct laser desorption ionization; electrospray ionization ceramides; sphingolipids; adjuvants; Fourier transform ion cyclotron resonance mass spectrometry (FTICR MS); nuclear magnetic resonance (NMR); direct laser desorption ionization; electrospray ionization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ross, C.W.; Simonsick, W.J.; Bogusky, M.J.; Celikay, R.W.; Guare, J.P.; Newton, R.C. Fourier Transform Mass Spectrometry and Nuclear Magnetic Resonance Analysis for the Rapid and Accurate Characterization of Hexacosanoylceramide. Int. J. Mol. Sci. 2016, 17, 1024.

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