627473-01-2Relevant academic research and scientific papers
Conformational study of the hydroxymethyl group in α-D-mannose derivatives
Nobrega, Chaxiraxi,Vazquez, Jesus T.
, p. 2793 - 2801 (2003)
A study of the dependence of the hydroxymethyl group in α-D-mannose derivatives on the aglycon and its absolute configuration was performed by means of circular dichroism (CD) and NMR data. Depending mainly on the aglycon present, the gg or the gt rotamer was the most populated, the tg rotamer having a small population. In addition, the study showed a correlation between the rotational populations and the aglycon, the population of the gt rotamer increasing as the pKa of the bonded alcohol (aglycon) increased. Furthermore, the results revealed a strong dependence on the absolute configuration of the aglycon and point to the stereoelectronic exo-anomeric effect being responsible for these rotational dependencies besides nonbonding interactions.
