J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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The Journal of Lipid Research, Vol. 40, 117-125, January 1999
Copyright © 1999 by Lipid Research, Inc.

Original Article

Chemical synthesis of D-ribo-phytosphingosine-1- phosphate, a potential modulator of cellular processes

Shengrong Lia, William K. Wilsona, and George J. Schroepfer, Jr.a
a Departments of Biochemistry and Cell Biology and of Chemistry, Rice University, 6100 Main St., Houston, TX 77005-1892

Correspondence to: George J. Schroepfer, Jr.

D-erythro -Sphingosine-1-phosphate (2), an intermediate in sphingosine metabolism, shows a diversity of biological activities. Comparable roles might be anticipated for D-ribo -phytosphingosine-1-phosphate (1). We describe an efficient three-step chemical synthesis of 1 from D-ribo -phytosphingosine. Our approach is based on standard phosphoramidite methodology and on the finding of Boumendjel and Miller (J. Lipid Res. 1994. 35: 2305–2311) that sphingosine can be monophosphorylated at the 1-hydroxyl without protection of the 3-hydroxyl. However, we were unable to duplicate their reported synthesis of 2 without important modifications in reagents and reaction conditions. Under the reported conditions for preparing 2, we obtained a cyclic carbamate (14), which we have isolated and identified. The structures of 1 and the cyclic carbamate 14 were elucidated by a combination of mass spectrometry and 1D and 2D nuclear magnetic resonance spectroscopy.—Li, S., W. K. Wilson, and G. J. Schroepfer, Jr. Chemical synthesis of D-ribo-phytosphingosine-1-phosphate, a potential modulator of cellular processes. J. Lipid. Res. 1999. 40: 117–125.

Supplementary key words: phytosphingosine-1-phosphate, sphingosine-1-phosphate, phosphorylation, NMR, mass spectrometry


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