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Because of its very asymmetric structure, the base brucine has long been used to resolve enantiomers of acidic moieties. Here, we have used it to bring about crystallization of an acidic disaccharide otherwise very resistant to crystallization. The disaccharide, containing a carboxylate groups in each octose monomer, was isolated from the lipopolysaccharide of the bacteria Burkholderia cepacia. It shows the substitution of Ko (D-glycero-D-talo-oct-2ulosonic acid) for the normal Kdo (3-deoxy-D-manno-oct-2-ulosonic acid). We have recrystallized it as its dibrucinium salt, a hexahydrate, in which the disaccharide and four of the water molecules are fully ordered. The orthorhombic cell [a = 12.987(2), b = 15.362(2), c = 33.590(5) Å] shows brucine layers normal to [001], which provide a suitable matrix for the incorporation of the disaccharide. The layer structure of brucine, shown in the diagram, is different from any we have encountered formerly.

Use of brucine to crystallise a disaccharide from a bacterial source