title: Total synthesis of an immunomodulatory phosphoglycolipid from thermophilic bacteria.
abstract: A method for the stereocontrolled synthesis of a bacterial phosphoglycolipid (PGL1) isolated from thermophilic bacteria is described. The key features of the synthesis include a highly α-selective glycosylation reaction between a trichloroacetimidate donor and a D-lyxose-derived primary alcohol acceptor and the late-stage incorporation of the phospholipid.
authors.affiliation: Department of Chemistry, National Tsing Hua University, No. 101, Section 2, Kuang Fu Road, Hsinchu 300, Taiwan.
authors.forename: Hong-Jyune
authors.initials: HJ
authors.lastname: Lin
authors.forename: Avijit Kumar
authors.initials: AK
authors.lastname: Adak
authors.forename: L Vijaya Raghava
authors.initials: LV
authors.lastname: Reddy
authors.forename: Shih-Hsiung
authors.initials: SH
authors.lastname: Wu
authors.forename: Chun-Cheng
authors.initials: CC
authors.lastname: Lin
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D062845:Chloroacetates / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D010429:Pentoses / Q000737:chemistry*; D010743:Phospholipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012821:Silanes / Q000737:chemistry; D013824:Thermus / Q000737:chemistry*
chemical_list: D000081:Acetamides; D000276:Adjuvants, Immunologic; D062845:Chloroacetates; D010429:Pentoses; D010743:Phospholipids; D012821:Silanes; C043333:lyxose; C009528:trichloroacetamide