|TUD Organische Chemie||Immel||Structures||CHIME - Sucrose (Informations)||View or Print (this frame only)|
Molecular Modeling of Saccharides, Part VII.
The Conformation of Sucrose in Water: a Molecular Dynamics Approach.
S. Immel and F. W. Lichtenthaler, Liebigs Ann. Chem. 1995, 1925-1937.
Sucrose, the "royal carbohydrate", has been the world's most abundantly produced organic compound, and this in paralleled purity. Here, its solid-state structure (with and without unit cell definitions), as well as some computer-generated geometries can be downloaded. Conformational analysis was carried out using the PIMM force-field, revealing three different energy-minimum conformations A - C, with increasing energy and differing intersaccharidic torsion angles. The global energy-minimum geometry (A) closely resembles the solid-state conformation. The geometries A and B co-exist in an approximate 2 : 1 ratio. The solution conformation of sucrose in water was investigated using molecular dynamics with explicit incorporation of water (sucrose in a truncated octahedron periodic box with 571 water molecules) and umbrella sampling techniques (GROMOS force-field). Based on these molecular modelings, we have outlined new entry reactions towards selectively modified sucrose derivatives as well as some structure-sweetness relationships for sucrose and its derivatives.