N.m.r. studies of the conformation of analogues of methyl beta-lactoside in methyl sulfoxide-d6.
The 1H- and 13C-n.m.r. spectra of solutions of methyl beta-lactoside (1), all of its monodeoxy derivatives (2, 3, 6-10), the 3-O-methyl derivative (4), and methyl 4-O-beta-D-galactopyranosyl-D-xylopyranoside (5) in methyl sulfoxide-d6 have been analysed. The n.O.e.'s and specific desheildings indicate similar distributions of low-energy conformers, comparable to those in aqueous solution. The major conformer has torsion angles phi H and psi H of 49 degrees and 5 degrees, respectively, with contributions of conformers with phi/psi 24 degrees/-59 degrees, 22 degrees/32 degrees, and 6 degrees/44 degrees.
Rivera-Sagredo
A
A
Grupo de Carbohidratos, Instituto de Química Orgánica, C.S.I.C., Madrid, Spain.
Jiménez-Barbero
J
J
Martín-Lomas
M
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides / Q000737:chemistry*; D008969:Molecular Sequence Data; D012996:Solutions / Q000737:chemistry; D014994:Xylose / Q000031:analogs & derivatives
D008759:Methylglycosides; D012996:Solutions; C034207:methyl lactoside; D014994:Xylose; D004121:Dimethyl Sulfoxide