, Volume 5, Issue 9, pp 782–785 | Cite as

A simple preparative procedure for the rapid isolation of phytosphingosine from the yeastHansenula ciferrii

  • Benjamin Weiss
  • Richard L. Stiller


Phytosphingosine and dihydrosphingosine were isolated as a mixture of their N-acetyl derivatives from the cells of the yeastHansenula ciferrii. After alkaline hydrolysis of the N-acetyl compounds, the free base mixture was reacted with either acetone orp-nitrobenzaldehyde. The reaction products consisting of the carbonyl derivative of phytosphingosine and free dihydrosphingosine were separated on an acetyl cellulose column. The acetone orp-nitrobenzaldehyde derivative of phytosphingosine recovered from the benzene eluate contained no dihydrosphingosine as determined by thin layer and gas liquid chromatography. The operating time from preparation of the derivative through column purification was less than 3 hrs. Mass spectrometry of the acetone andp-nitrobenzaldehyde derivatives disclosed in each case that ring closure with the carbonyl reagent involved the amino and primary hydroxyl groups to giveD-ribo-2-dimethyl-4-(2,3-dihydroxyhexadecyl) oxazolidine andD-ribo-2-p-nitrophenyl-4-(2,3-dihydroxyhexadecyl) oxazolidene, respectively.


Sphingosine Sulfate Salt Silicic Acid Column Nitrobenzaldehyde Oxazolidine 
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  1. 1.
    Greene, M.L., T. Kaneshiro and J.H. Law, Biochim. Biophys. Acta 98: 582 (1965).PubMedGoogle Scholar
  2. 2.
    Wickerham, L.J., and F.H. Stodola, J. Bacteriol. 80: 484 (1960).PubMedGoogle Scholar
  3. 3.
    Stodola, F.H., L.J. Wickerham, C.R. Scholfield and H.J. Button, Arch. Biochem. Biophys. 98: 176 (1962).CrossRefGoogle Scholar
  4. 4.
    Stodola, F.H., and L.J. Wickerham, J. Biol. Chem. 235: 2584 (1960).Google Scholar
  5. 5.
    Barenholz, Y., and S. Gatt, Biochim. Biophys. Acta 152: 790 (1968).PubMedGoogle Scholar
  6. 6.
    Reindel, F., A. Weickmann, S. Picard, K. Luber and P. Turula, Ann. Chem. 544: 116 (1940).Google Scholar
  7. 7.
    Carter, H.E., W.D. Celmer, W.E.M. Lands, K.L. Mueller and H.H. Tomizawa, J. Biol. Chem. 206: 613 (1954).PubMedGoogle Scholar
  8. 8.
    Weiss, B., and R.L. Stiller, J. Lipid Res. 6: 159 (1965).PubMedGoogle Scholar
  9. 9.
    Sambasivarao, K., and R.H. McCluer, Ibid. 4: 437 (1963).Google Scholar
  10. 10.
    Carter, H.E., and R.C. Gaver, J. Lipid Res. 8: 391 (1967).PubMedGoogle Scholar

Copyright information

© American Oil Chemists’ Society 1969

Authors and Affiliations

  • Benjamin Weiss
    • 1
  • Richard L. Stiller
    • 1
  1. 1.Division of Neuroscience, N.Y. State Psychiatric Institute and Department of Biochemistry, College of Physicians and SurgeonsColumbia UniversityNew York

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