The purpose of the proposed research to thoroughly understand the basis for chiral recognition between enantiomeric compounds and derivatized or underivatized cyclodextri and then to use this knowledge in a variety of practical and esoteric ways. The interaction of diastereomers and even structural isomers with cyclodextrin based substrates will be considered as well. Three important applications of this work are: the efficient separation of enantiomeric compounds, the determination of absolute configuration by chromatographic means, and the rapid and sensitive determination of optical purity. The importance of this work to the medical and health sciences becomes clear when one realizes that over half of the top 200 prescribed drugs in the United States contain at least one chiral center. Furthermore, it is well known that drug isomers frequently have different physiological properties. A variety of derivatized and underivatized cyclodextrins will be made or isolated and attached to a variety of supports. This will result in a chiral stationary phase that is capable of forming inclusion complexes with several molecules. Interaction energies will be calculated between the cyclodextrins and a variety of chiral model compounds and currently used pharmaceutical compounds. Separation efficiency and resolution of these enantiomeric compounds on different cyclodextrin based packings will be evaluated as well. It is expected that the proposed theoretical and mechanistic work will compliment the more practical analytical and preparative separation methods developed in this study.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
7R01GM036292-03
Application #
3289972
Study Section
Metallobiochemistry Study Section (BMT)
Project Start
1987-09-01
Project End
1989-03-31
Budget Start
1987-09-01
Budget End
1988-03-31
Support Year
3
Fiscal Year
1987
Total Cost
Indirect Cost
Name
University of Missouri-Rolla
Department
Type
Schools of Arts and Sciences
DUNS #
804883767
City
Rolla
State
MO
Country
United States
Zip Code
65409
Peter, A; Torok, G; Armstrong, D W (1998) High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase. J Chromatogr A 793:283-96
Armstrong, D W; Gasper, M P; Rundlett, K L (1995) Highly enantioselective capillary electrophoretic separations with dilute solutions of the macrocyclic antibiotic ristocetin A. J Chromatogr A 689:285-304
Berthod, A; Zhou, E Y; Le, K et al. (1995) Determination and use of Rohrschneider-McReynolds constants for chiral stationary phases used in capillary gas chromatography. Anal Chem 67:849-57
Pawlowska, M; Zukowski, J; Armstrong, D W (1994) Sensitive enantiomeric separation of aliphatic and aromatic amines using aromatic anhydrides as nonchiral derivatizing agents. J Chromatogr A 666:485-91
Armstrong, D W; Rundlett, K; Reid 3rd, G L (1994) Use of a macrocyclic antibiotic, rifamycin B, and indirect detection for the resolution of racemic amino alcohols by CE. Anal Chem 66:1690-5
Pawlowska, M; Armstrong, D W (1994) Evaluation of enantiomeric purity of selected amino acids in honey. Chirality 6:270-6
Armstrong, D W; Rundlett, K L; Chen, J R (1994) Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis. Chirality 6:496-509
Rundlett, K L; Armstrong, D W (1994) Evaluation of free D-glutamate in processed foods. Chirality 6:277-82
Zukowski, J; Pawlowska, M; Nagatkina, M et al. (1993) High-performance liquid chromatographic enantioseparation of glycyl di- and tripeptides on native cyclodextrin bonded phases. Mechanistic considerations. J Chromatogr 629:169-79
Armstrong, D W; Gasper, M; Lee, S H et al. (1993) D-amino acid levels in human physiological fluids. Chirality 5:375-8

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