The structure of O-phospho-DL-threonine in potassium, sodium and ammonium environments

Abstract

Summary Interactions of O-phospho-DL-threonine (DL-PThr) in the different ionization states with potassium, sodium and ammonium cations have been studied on five crystals (denoted as I-V). In semipotassium salt of DL-PThr (I), the phosphate group adopts the nearly trans conformation, whereas in mono- and disodium salts (II and III) and in mono- and diammonium salts of DL-PThr (IV and V) the phosphate group is situated anticlinal to the rest of the molecule, showing its conformational flexibility depending on the crystal environment, where significant differences are observed in interactions of K+, Na+ and NH4 + cations with PThr. The crystal packing in each of I-V is dominated by interactions between PThr moieties and the cations and hydrogen bond networks involving the phosphate, carboxyl, and amino groups of PThr moieties and water molecules. In crystal I, water molecules are not involved in potassium cation complexation. In crystals II and III, sodium cations show a preference for water molecules over PThr anions as ligands in coordination spheres. Especially in crystals I-III, water molecules are involved in very extensive networks of hydrogen-bond interactions.