Facile synthesis of a library of Lyme disease glycolipid antigens.
A library of one of the two Lyme disease antigens, BbGL1, has been synthesized in four steps from D-galactose using BF(3)-promoted glycosylation of the peracetate to introduce the cholesteryl β-glycoside and TBTU-promoted esterification to add a range of fatty acids regioselectively at O-6 of D-galactose in good yield.
Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. Box 15000, Halifax, NS, Canada B3H 4R2.
Jean-d'Amour K
JD
Twibanire
Raha Parvizi
RP
Omran
T Bruce
TB
Grindley
D025065:Borrelia burgdorferi / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D006801:Humans; D008193:Lyme Disease / Q000276:immunology*; D015394:Molecular Structure; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology; D013237:Stereoisomerism
D006017:Glycolipids; D012503:Saponins; C475929:cholesteryl 6-O-palmitoylgalactopyranoside; D005690:Galactose