Synthetic receptor analogues: the conformation of methyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside) and related derivatives, determined by n.m.r. and computational methods.
The conformations of galabiose and its methyl and ethyl beta-glycosides as well as the 3-deoxy, 3-O-methyl, 3-deoxy-3-C-methyl, 3-deoxy-3-C-ethyl, and 6-deoxy analogues were investigated by n.m.r. (1H, 13C, n.O.e.) and computational (HSEA) methods. A good correlation was found between the computational data and the n.m.r. data for aqueous solutions. The conformations in aqueous solution were similar, whereas crystalline galabiose or methyl beta-D-galabioside in solution in methyl sulfoxide adopted different conformations that showed intramolecular hydrogen bonds (O-5'. . . O-3 and O-2'. . . O-6, respectively).
Department of Organic Chemistry, Technical University of Denmark, Lyngby.
K
K
Bock
T
T
Frejd
J
J
Kihlberg
G
G
Magnusson
D002151:Calorimetry; D002236:Carbohydrate Conformation; D004187:Disaccharides; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008722:Methods; D008756:Methylgalactosides; D008759:Methylglycosides; D008958:Models, Molecular; D010127:P Blood-Group System; D011971:Receptors, Immunologic; D013329:Structure-Activity Relationship
D004187:Disaccharides; D008756:Methylgalactosides; D008759:Methylglycosides; D010127:P Blood-Group System; D011971:Receptors, Immunologic; C032103:4-O-alpha-D-galactopyranosyl-D-galactose; C057031:methyl 4-O-galactopyranosylgalactopyranoside