title: Impact of sugar stereochemistry on natural killer T cell stimulation by bacterial glycolipids.
abstract: Natural killer T (NKT) cells recognize glycolipids produced by Sphingomonas bacteria, and these glycolipids contain C6-oxidized sugars, either glucuronic acid or galacturonic acid, linked to ceramides. Glycolipids with gluco stereochemistry are the most prevalent. Multiple studies have demonstrated that galactosylceramides are more potent stimulators of NKT cells than their glucose isomers. To determine if this stereoselectivity is retained in the context of the C6-oxidized sugars found in bacterial glycolipids, we prepared two sets of gluco and galacto-glycolipids oxidized at their C6 positions and compared their NKT stimulatory properties. In the context of carboxylic acid groups at C6, gluco stereochemistry gave the more potent responses. We also prepared bacterial glycolipids containing more complex ceramide groups to determine if these chains impact NKT cell responses.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, USA.
authors.forename: Shenglou
authors.initials: S
authors.lastname: Deng
authors.forename: Jochen
authors.initials: J
authors.lastname: Mattner
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Zang
authors.forename: Li
authors.initials: L
authors.lastname: Bai
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: D000818:Animals; D000942:Antigens, Bacterial / Q000737:chemistry / Q000276:immunology; D003713:Dendritic Cells / Q000187:drug effects* / Q000276:immunology; D004797:Enzyme-Linked Immunosorbent Assay; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000276:immunology* / Q000494:pharmacology; D005963:Glucosylceramides / Q000138:chemical synthesis / Q000276:immunology* / Q000494:pharmacology; D020723:Glucuronic Acid / Q000737:chemistry / Q000276:immunology; D006603:Hexuronic Acids / Q000737:chemistry / Q000276:immunology; D007113:Immunity, Innate / Q000187:drug effects; D007371:Interferon-gamma / Q000032:analysis / Q000096:biosynthesis; D015847:Interleukin-4 / Q000032:analysis / Q000096:biosynthesis; D007536:Isomerism; D008213:Lymphocyte Activation / Q000187:drug effects* / Q000276:immunology; D051379:Mice; D008815:Mice, Inbred Strains; D055611:Natural Killer T-Cells / Q000187:drug effects* / Q000276:immunology; D020578:Sphingomonas / Q000737:chemistry / Q000276:immunology; D013154:Spleen / Q000166:cytology / Q000187:drug effects* / Q000276:immunology
chemical_list: D000942:Antigens, Bacterial; D005699:Galactosylceramides; D005963:Glucosylceramides; D006603:Hexuronic Acids; D015847:Interleukin-4; C007819:galacturonic acid; D007371:Interferon-gamma; D020723:Glucuronic Acid