Synthesis and absolute structures of Mycoplasma pneumoniae beta-glyceroglycolipid antigens.
Just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1-->6)-linked disaccharide structure close to each other; one has beta-d-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-d-glucopyranoside (beta-Glc-type 2). In the present study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. (1)H NMR and TLC-immunostaining studies of the synthetic compounds enable us to establish the absolute structures having the beta-(1-->6)-linked disaccharides at the glycerol sn-3 position.
Miyachi
Akira
A
Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
Miyazaki
Atsushi
A
Shingu
Yuko
Y
Matsuda
Kazuhiro
K
Dohi
Hirofumi
H
Nishida
Yoshihiro
Y
D000942:Antigens, Bacterial / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009177:Mycoplasma pneumoniae / Q000737:chemistry* / Q000276:immunology
D000942:Antigens, Bacterial; D006017:Glycolipids