出版社：American Society for Biochemistry and Molecular Biology
摘要：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.
关键词：phytosphingosine-1-phosphate ; sphingosine-1-phosphate ; phosphorylation ; NMR ; mass spectrometry
