title: Synthesis of diglycosylceramides and evaluation of their iNKT cell stimulatory properties.
abstract: Stimulation of iNKT cells is highly dependent on the structures of the glycolipids presented by CD1d. Furthermore, antigen processing and CD1d loading in lysosomes play central roles in controlling the stimulatory properties of glycolipid antigens. Previously, we determined that substitution at C6'' on alpha-galactosylceramides did not significantly impact stimulatory properties; however, it was not known if substitution at this position influenced lysosomal processing of oligoglycosylceramides. We have prepared a series of mono- and di-galactosylceramides to observe the impact of C6'' substitution on glycosidase truncation of these glycolipids. We found that substitution did not significantly impact glycosidase activity or loading into CD1d.
authors.affiliation: Department of Chemistry and Biochemistry, C100 BNSN, Brigham Young University, Provo, UT 84602, USA.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.forename: Shenglou
authors.initials: S
authors.lastname: Deng
authors.forename: Li
authors.initials: L
authors.lastname: Bai
authors.forename: Stefan
authors.initials: S
authors.lastname: Freigang
authors.forename: Jochen
authors.initials: J
authors.lastname: Mattner
authors.forename: Luc
authors.initials: L
authors.lastname: Teyton
authors.forename: Albert
authors.initials: A
authors.lastname: Bendelac
authors.forename: Paul B
authors.initials: PB
authors.lastname: Savage
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D017951:Antigen Presentation / Q000187:drug effects / Q000276:immunology; D018949:Antigens, CD1 / Q000378:metabolism; D055610:Antigens, CD1d; D002478:Cells, Cultured; D003713:Dendritic Cells / Q000276:immunology; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000187:drug effects / Q000378:metabolism; D006825:Hybridomas / Q000276:immunology; D007694:Killer Cells, Natural / Q000187:drug effects* / Q000276:immunology*; D008247:Lysosomes / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000276:Adjuvants, Immunologic; D018949:Antigens, CD1; D055610:Antigens, CD1d; D005699:Galactosylceramides; D006026:Glycoside Hydrolases; C103873:KRN 7000