Conformation of methylated amino acids: structure of 3,4-dimethoxy-alpha-methyl-DL-phenylalanine sesquihydrate.
C12H17NO4.1.5H2O, Mr = 266.3, triclinic, P1, a = 5.872 (1), b = 11.437 (2), c = 20.434 (1) A, alpha = 95.74 (1), beta = 96.91 (1), gamma = 89.18 (1) degrees, V = 1355.5 A3, Z = 4, Dm = 1.29, D chi = 1.305 g cm-3, lambda(Cu K alpha) = 1.5418 A, mu = 8.3 cm-1, F(000) = 572, T = 294 K, R = 0.038 for 4006 reflections, I greater than or equal to 3 sigma(I). Both the molecules A and B in the asymmetric unit exist as zwitterions. With respect to the D enantiomer, the torsion angles psi 1 and psi 2 are +47.2 and -134.4 degrees in molecule A and +33.3 and -147.5 degrees in molecule B respectively. The torsion angles of the alpha-methyl group, NH3+ and COO- groups with respect to Cv are in molecules A and B respectively +67.2, +66.8, -174.3, -175.6, and -59.2 and -59.5 degrees. The hydrogen-bonding environment of water OW1 is trigonal nonplanar; OW2 is trigonal planar and OW3 is tetrahedral. The crystal structure is stabilized by a number of hydrogen bonds involving the amino and carboxylate groups of both molecules A and B and the water molecules.
Srikrishnan
T
T
Center for Crystallographic Research, Roswell Park Memorial Institute, Buffalo, New York 14263.
Ravichandran
V
V
Chacko
K K
KK
D003198:Computer Simulation; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives*
C062533:3,4-dimethoxy-alpha-methylphenylalanine; D010649:Phenylalanine