Chiral discrimination in cyclodextrin complexes of amino acid derivatives: beta-cyclodextrin/N-acetyl-L-phenylalanine and N-acetyl-D-phenylalanine complexes.
In a systematic study of molecular recognition of amino acid derivatives in solid-state beta-cyclodextrin (beta-CD) complexes, we have determined crystal structures for complexes of beta-cyclodextrin/N-acetyl-L-phenylalanine at 298 and 20 K and for N-acetyl-D-phenylalanine at 298 K. The crystal structures for the N-acetyl-L-phenylalanine complex present disordered inclusion complexes for which the distribution of guest molecules at room temperature is not resolvable; however, they can be located with considerable confidence at low temperature. In contrast, the complex with N-acetyl-D-phenylalanine is well ordered at room temperature. The latter complex presents an example of a complex in this series in which a water molecule is included deeply in the hydrophobic torus of the extended dimer host. In an effort to understand the mechanisms of molecular recognition giving rise to the dramatic differences in crystallographic order in these crystal structures, we have examined the intermolecular interactions in detail and have examined insertion of the enantiomer of the D-complex into the chiral beta-CD complex crystal lattice.
Alexander
Jennifer M
JM
Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA.
Clark
Joanna L
JL
Brett
Tom J
TJ
Stezowski
John J
JJ
D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003505:Cyclodextrins / Q000737:chemistry*; D019281:Dimerization; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008958:Models, Molecular; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D013696:Temperature; D047392:beta-Cyclodextrins
D000596:Amino Acids; D003505:Cyclodextrins; D047392:beta-Cyclodextrins; D010649:Phenylalanine; C031215:betadex; C044228:N-acetylphenylalanine