title: The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose.
abstract: The total synthesis of absolute anomeric confirmation α-galactosylceramide analogues from raffinose is described. Using the naturally occurring α-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical α-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new α-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.
authors.affiliation: College of Pharmacy, Nankai University, Tianjin 300071, China.
authors.forename: Zhenxing
authors.initials: Z
authors.lastname: Zhang
authors.forename: Wei
authors.initials: W
authors.lastname: Zhao
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Xia
authors.forename: Wenpeng
authors.initials: W
authors.lastname: Zhang
authors.forename: Peng George
authors.initials: PG
authors.lastname: Wang
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011887:Raffinose / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; C493154:alpha-galactosylceramide; D011887:Raffinose