title: Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4'-epi-C-Glycoside of KRN7000.
abstract: A new immunostimulant, the 4'-epimer of α-C-GalCer, was synthesized from a C2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.
authors: Institute of Biomedical Sciences, Academia Sinica , No. 128 Academia Road, Section 2, Nankang, Taipei, Taiwan 11529.
authors: Ya-Jen
authors: YJ
authors: Chang
authors: Department of Chemistry, National Central University , No. 300 Jhong-Da Road, Jhong-li, Taoyuan, Taiwan 32001.
authors: Yi-Chen
authors: YC
authors: Hsuan
authors: Institute of Biomedical Sciences, Academia Sinica , No. 128 Academia Road, Section 2, Nankang, Taipei, Taiwan 11529.
authors: Alan Chuan-Ying
authors: AC
authors: Lai
authors: Institute of Biomedical Sciences, Academia Sinica , No. 128 Academia Road, Section 2, Nankang, Taipei, Taiwan 11529.
authors: Yun-Chiann
authors: YC
authors: Han
authors: Department of Chemistry, National Central University , No. 300 Jhong-Da Road, Jhong-li, Taoyuan, Taiwan 32001.
authors: Duen-Ren
authors: DR
authors: Hou
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001388:Aziridines / Q000737:chemistry*; D002301:Cardiac Glycosides; D016207:Cytokines; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides; D008386:Marine Biology; D051379:Mice; D008807:Mice, Inbred BALB C; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D055611:Natural Killer T-Cells; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000276:Adjuvants, Immunologic; D001388:Aziridines; C550181:C-galactosylceramide; C438934:C-glycoside; D002301:Cardiac Glycosides; D016207:Cytokines; D005699:Galactosylceramides; D006027:Glycosides; D009005:Monosaccharides; C493154:alpha-galactosylceramide; C103873:KRN 7000