Synthesis and absolute structures of Mycoplasma pneumoniae β-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. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.