Collect. Czech. Chem. Commun. 1979, 44, 174-182

Conformation of 3-acetamido-3,6-dideoxyhexopyranosides: Circular dichroism study

Slavomír Bystrickýa, Ivo Fričb, Jan Staněkc, Karel Čapekc, Jiří Jarýc and Karel Bláhab

a Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
c Laboratory of Monosaccharides, Prague Institute of Chemical Technology, 166 28 Prague 6


CD spectra of 15 stereoisomeric methyl 3-acetamido-3,6-dideoxyhexopyranosides were measured in methanol, 2,2,2-trifluoroethanol and acetonitrile. The data have been applied for estimation of probable conformations. The factor determining signs of the observed Cotton effects seems to be the spatial orientation of the acetamido group with respect to the pyranose ring. The possible role of a non-planar amide group is also discussed.