Chemical synthesis of cholesteryl beta-D-galactofuranoside and -pyranoside.
Two isomeric cholesteryl galactosides, cholesteryl beta-D-galactofuranoside and -pyranoside, have been synthesized by the Koenigs-Knorr reaction. Glycosylation of cholesterol with 2,3,5,6-tetra-O-benzoyl-D-galactofuranosyl bromide, followed by Zemplén saponification with sodium methoxide, gave cholesteryl beta-D-galactofuranoside. By using 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl bromide as the glycosyl donor, followed by alkaline hydrolysis, cholesteryl beta-D-galactopyranoside was obtained. The title compounds were characterized by their IR spectra and by their (1)H and (13)C NMR spectra. Structure considerations of the two cholesteryl galactosides correlated with data in the literature, thus confirming that cholesteryl beta-D-galactopyranoside is an antigenic lipid of Lyme disease agent, Borrelia burgdorferi.
Iga
Dumitru Petru
DP
University of Bucharest, Faculty for Biology, Splaiul Independentei 95, Bucuresti 5 R-76201, Romania. pdiga49@yahoo.com
Iga
Silvia
S
Schmidt
Richard R
RR
Buzas
Maria-Cristina
MC
D000942:Antigens, Bacterial / Q000737:chemistry; D025065:Borrelia burgdorferi / Q000737:chemistry / Q000276:immunology; D002784:Cholesterol / Q000737:chemistry*; D012503:Saponins / Q000138:chemical synthesis*
D000942:Antigens, Bacterial; D012503:Saponins; D002784:Cholesterol