Circular Dichroic Studies of 2-Amino-2-deoxy-galactopyranosides - Conformations of the 2-(N-Acetyl-p-bromobenzamido) Group

Article abstract of DOI:10.1016/S0957-4166(00)86076-0

The CD spectra of methyl 2-amino-2-deoxy-D-galactopyranoside mono-N-acylates (acetyl or p-bromobenzoyl) resemble those of the corresponding O-acylates and can be accounted for by the additivity rule.However, the CD of pyranosides containing the N-acetyl-p-bromobenzamido imide group (NAcBz) are far more complex than those of mono-N-acylates and their O-counterparts, and furthermore, the solvent- and temperature-dependent changes differ for the α- and β-anomers.These differences can be accounted for by the different conformations of the 2-NAcBz group.