title: Divergent syntheses of all stereoisomers of phytosphingosine and their use in the construction of a ceramide library.
abstract: 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.
authors.affiliation: Department of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea.
authors.forename: Jeong-Ju
authors.initials: JJ
authors.lastname: Park
authors.forename: Ji Hyung
authors.initials: JH
authors.lastname: Lee
authors.forename: Qian
authors.initials: Q
authors.lastname: Li
authors.forename: Kristine
authors.initials: K
authors.lastname: Diaz
authors.forename: Young-Tae
authors.initials: YT
authors.lastname: Chang
authors.forename: Sung-Kee
authors.initials: SK
authors.lastname: Chung
mesh_terms: 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
chemical_list: D002518:Ceramides; C012491:phytosphingosine; D013110:Sphingosine