Mutarotation

In stereochemistry, mutarotation is the change in optical rotation of a chiral material in a solution due to a change in proportion of the two constituent anomers (i.e. the interconversion of their respective stereocenters) until equilibrium is reached. Cyclic sugars show mutarotation as α and β anomeric forms interconvert.[1] The optical rotation of the solution depends on the optical rotation of each anomer and their ratio in the solution.

Mutarotation was discovered by French chemist Augustin-Pierre Dubrunfaut in 1844, when he noticed that the specific rotation of aqueous sugar solution changes with time.[2][3]

  1. ^ IUPAC Gold Book mutarotation
  2. ^ Derek Horton (2008). "The Development of Carbohydrate Chemistry and Biology". Carbohydrate Chemistry, Biology and Medical Applications: 1–28. doi:10.1016/B978-0-08-054816-6.00001-X. ISBN 9780080548166.
  3. ^ Fletcher Hewitt G (1940). "Augustin-Pierre Dubrunfaut—An early sugar chemist". Journal of Chemical Education. 17 (4): 153. Bibcode:1940JChEd..17..153F. doi:10.1021/ed017p153.