For example, the sugars α-glucose and β-glucose are epimers. In α-glucose, the -OH group on the first (anomeric) carbon is in the direction opposite the methylene group (in the axial position). In β-glucose, the -OH group is oriented in the same direction as the methylene group (in the equatorial position). These two molecules are both epimers and anomers.
In this case, β-D-glucopyranose and β-D-mannopyranose are epimers because they differ only in the stereochemistry at the 2 position. The hydroxyl group in β-D-glucopyranose is equatorial (in the "plane" of the ring) while in β-D-mannopyranose the 2 hydroxyl group is axial (up from the "plane" of the ring). These two molecules are epimers but not anomers.
In chemical nomenclature, one of the epimeric pairs is given the prefix epi- for example in quinine and epi-quinine. When the pairs are enantiomers, the prefix becomes ent-.
Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)- 209B , (-)- 231C , (-)- 233D , (-)- 235B" , (-)- 221I , and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors.(Full Research Paper)
Sep 28, 2007; Authors: Soushi Kobayashi ; Naoki Toyooka (corresponding author) ; Dejun Zhou ; Hiroshi Tsuneki ; Tsutomu Wada ;...