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Title
  • en Synthesis of Urethane Derivatives of Mono- and Diacylglycerols for Use as HPLC Standards in the Enantiomeric Separation
Creator
    • en Tada, Naoto
    • en Fujita, Honami
Accessrights open access
Rights
  • en The final publication is available at www.springerlink.com
Subject
  • Other en 3,5-Dinitrophenylurethane
  • Other en 1-(1-Naphthyl)ethyl urethane
  • Other en Triacylglycerol
  • Other en Diacylglycerol
  • Other en Monoacylglycerol
  • Other en Enantiomer
  • Other en Diastereomer
  • Other en HPLC
  • Other en Stereospecific analysis
  • NDC 660
Description
  • Abstract en 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.
Publisher en Springer
Date
    Issued2014-07
Language
  • eng
Resource Type journal article
Version Type AM
Identifier HDL http://hdl.handle.net/2115/59450
Relation
  • isVersionOf DOI https://doi.org/10.1007/s11746-014-2452-z
Journal
    • PISSN 0003-021X
    • NCID AA00692919
      • en Journal of The American Oil Chemists Society
      • Volume Number91 Issue Number7 Page Start1131 Page End1137
File
Oaidate 2023-07-26