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Interactions of  O -phospho-DL-threonine (DL- P Thr) 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- P Thr ( 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- P Thr ( 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 NH 4  +  cations with  P Thr. The crystal packing in each of  I-V  is dominated by interactions between  P Thr moieties and the cations and hydrogen bond networks involving the phosphate, carboxyl, and amino groups of  P Thr 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  P Thr anions as ligands in coordination spheres. Especially in crystals  I-III , water molecules are involved in very extensive networks of hydrogen-bond interactions.

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