title: Total synthesis of a glycoglycerolipid from Meiothermus taiwanensis through a one-pot glycosylation reaction and exploration of its immunological properties.
abstract: The total synthesis of a glycoglycerolipid isolate of Meiothermus taiwanensis and its truncated structural analogues is reported. Our synthesis employed DMF-modulated and low-concentration glycosylation reactions for the construction of α- and β-glycosidic bonds in the absence of participating protecting groups. Further simplification of the synthesis was achieved by employing a low-concentration one-pot glycosylation procedure. Preliminary immunological studies showed that one of the truncated structural analogues suppressed the cytokine production of THP-1 monocytes.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University (NCTU), SB 533, Science building II, 1001, Ta Hsueh Road, Hsinchu (Taiwan), Fax: (+886) 3-5723764.
authors.forename: Bhaswati
authors.initials: B
authors.lastname: Ghosh
authors.forename: Yen-Hsun
authors.initials: YH
authors.lastname: Lai
authors.forename: Yu-Yin
authors.initials: YY
authors.lastname: Shih
authors.forename: Tapan Kumar
authors.initials: TK
authors.lastname: Pradhan
authors.forename: Chun-Hung
authors.initials: CH
authors.lastname: Lin
authors.forename: Kwok-Kong Tony
authors.initials: KK
authors.lastname: Mong
mesh_terms: D002460:Cell Line; D016207:Cytokines / Q000096:biosynthesis / Q000187:drug effects / Q000276:immunology; D034301:Deinococcus / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology*; D006031:Glycosylation; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
chemical_list: D016207:Cytokines; D006017:Glycolipids; D008070:Lipopolysaccharides; C015903:glycerolglycolipids
keywords: glycosylation; immunology; lipids; natural products; total synthesis