Studies on crystalline complexes involving amino acids. V. The structure of L-serine-L-ascorbic acid

Abstract

L-Serine-L-ascorbic acid, C₃H₇NO₃· C₆H₈O₆, a 1:1 complex between the amino acid serine and the vitamin ascorbic acid, crystallizes in the orthorhombic space group P2₁2₁2₁ with four formula units in a cell of dimensions a= 5.335(3), b = 8.769(2), c = 25.782 (5) Å. The structure was solved by direct methods and refined by full-matrix least squares to an R of 0.036 for 951 observed reflections. Both molecules are neutral in the structure. The conformation of the serine molecule is different from that observed in the crystal structures of L-serine, DL-serine and L-serine monohydrate. The enediol group in the ascorbic acid molecule is planar, whereas significant departures from planarity are observed in the lactone group. The conformation of this molecule is similar to that observed in arginine ascorbate. The unlike molecules aggregate into separate columns in the crystal structure. The columns are held together by hydrogen bonds. Among these, a pair of hydrogen bonds between the enediol group of ascorbic acid and the carboxylate group of serine provides a possible model for a specific interaction between ascorbic acid and a carboxylate ion.