The conformation of 1,6-anhydrolactose and its hexa-acetate in solution

Carbohydr Res. 1991 Aug 20;215(2):239-50. doi: 10.1016/0008-6215(91)84024-9.

Abstract

The conformation of 1,6-anhydrolactoase (1) has been investigated by n.m.r. spectroscopy and molecular mechanics calculations. For a solution in D2O, the 1,6-anhydroglucopyranoid ring has a 1C4 conformation, whereas there is a approximately 1:1 equilibrium between the 1C4 and the BO,3 conformations in (CD3)2SO. There is restricted flexibility with phi -80 +/- 20 degrees and psi -120 +/- 40 degrees. The hexa-acetate (2) of 1 shows a similar conformational behaviour.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Lactose / analogs & derivatives*
  • Lactose / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Sequence Data
  • Optical Rotation

Substances

  • 1,6-anhydrolactose hexaacetate
  • 1,6-anhydrolactose
  • Lactose