Title |
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Synthesis of Urethane Derivatives of Mono- and Diacylglycerols for Use as HPLC Standards in the Enantiomeric Separation
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Creator |
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Accessrights |
open access |
Rights |
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The final publication is available at www.springerlink.com
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Subject |
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Other
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3,5-Dinitrophenylurethane
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Other
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1-(1-Naphthyl)ethyl urethane
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Other
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Triacylglycerol
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Other
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Diacylglycerol
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Other
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Monoacylglycerol
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Other
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Enantiomer
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Other
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Diastereomer
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Other
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HPLC
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Other
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Stereospecific analysis
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NDC
660
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Description |
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Abstract
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This paper presents a convenient method for the preparation of reference standards for high-performance liquid chromatography (HPLC) used in stereospecific analysis of triacyl-sn-glycerols via monoacylglycerol or diacylglycerol intermediates. In the analysis, these partial acylglycerols are separated into their respective positional and enantiomeric isomer classes by chiral HPLC as their 3,5-dinitrophenylurethane derivatives or by silicic acid HPLC as their (S)- or (R)-1-(1-naphthyl)ethyl urethane derivatives. In this study, these urethane derivative standards were synthesized by the following novel procedure: first, partial urethane derivatives of glycerol were prepared by carbamoylation of glycerol with isocyanates; secondly, the products were separated into positional isomer classes by silicic acid HPLC, and; finally, a fatty acid was added to the partial urethanes using N,N'-dicyclohexylcarbodiimide. The identities of the resulting urethane derivatives of glycerol were verified by mass spectrometry and HPLC. This new procedure is advantageous in that standard urethane derivatives of partial acylglycerols can be synthesized from no more than 50 mu g of fatty acids. This benefit is especially important in the case of rare and expensive fatty acids, such as very long chain polyunsaturated fatty acids, tetracosahexaenoic acid, and hexacosaheptaenoic acid, found in marine lipids.
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Publisher |
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Springer
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Date |
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Language |
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Resource Type |
journal article |
Version Type |
AM |
Identifier |
HDL
http://hdl.handle.net/2115/59450
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Relation |
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isVersionOf
DOI
https://doi.org/10.1007/s11746-014-2452-z
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Journal |
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PISSN
0003-021X
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NCID
AA00692919
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Journal of The American Oil Chemists Society
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Volume Number91
Issue Number7
Page Start1131
Page End1137
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File |
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Oaidate |
2023-07-26 |