Divergent syntheses of all stereoisomers of phytosphingosine and their use in the construction of a ceramide library.
Sphingolipids such as ceramide and sphingosine-1-phosphate have recently attracted intense research interests because of their functional roles as signaling molecules in many important physiological processes, such as growth arrest, apoptosis, and inflammatory responses, and cell proliferation, vascular maturation and trafficking of lymphocytes. The well-defined modular structures of ceramides and related glycosylceramides are ideally amenable to library formation for medicinal chemistry investigation. We have developed divergent synthetic routes to all eight phytosphingosine stereoisomers and then proceeded to prepare phytosphingosine-based ceramide library composed of more than 500 compounds.
Park
Jeong-Ju
JJ
Department of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea.
Lee
Ji Hyung
JH
Li
Qian
Q
Diaz
Kristine
K
Chang
Young-Tae
YT
Chung
Sung-Kee
SK
D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry; D002853:Chromatography, Liquid; D002855:Chromatography, Thin Layer; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D002518:Ceramides; C012491:phytosphingosine; D013110:Sphingosine