Theoretical study on conformation and stability of trehalose

Abstract

Trehalose is a non-reducing disaccharide composed of two α-(D)-glucose units linked together by a 1,1-glycosidic linkage. Trehalose has a number of conformers because it has 12 independent dihedral angles, which include the conformations of 8 OH groups, of the glycosidic linkage, and of CH₂OH groups. The relative stabilities of conformations of the disaccharide depend on the intramolecular hydrogen bond networks. In this work, we clarify stable conformers of trehalose using MP2 level of ab initio MO theory. We find out that the relative stabilities of conformers of trehalose depend on the conformation of glycosidic linkage. The most stable conformer of trehalose is composed of the most stable conformer of α-glucose held together by a 1,1-glycosidic linkage.