Abstract

Macrocyclic antibiotics are the newest and fastest growing class of chiral selectors for enantiomeric separations. Enantiomeric separation and evaluation are now mandated by the Food and Drug Administration for all pharmaceutical compounds that can exist as racemic modifications. Approximately 75 percent of all pharmaceutical products are chiral. Currently the mechanism(s) by which macrocyclic antibiotics achieve chiral recognition and enantioselective separation is unknown. There are three basic aims/objectives to this proposed work. They are: (1) elucidate the chiral recognition/enantioselective separation mechanism specifically for the glycopeptide antibiotics. (2) Synthesize and evaluate a new type of very simple macrocyclic glycopeptide (note that all known macrocyclic glycopeptides are produced biologically), and (3) Evaluate two unique, anionic-boron containing macrocyclic antibiotics. This work should greatly expand our understanding of these important compounds as well as their utility in the enantiomeric separation of biologically important molecules.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM053825-07
Application #
6386248
Study Section
Special Emphasis Panel (ZRG1-BMT (01))
Program Officer
Edmonds, Charles G
Project Start
1996-03-05
Project End
2003-12-31
Budget Start
2002-01-01
Budget End
2002-12-31
Support Year
7
Fiscal Year
2002
Total Cost
$233,456
Indirect Cost

  Institution

Name
Iowa State University
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
City
Ames
State
IA
Country
United States
Zip Code
50011

  Publications

Aranyi, Anita; Ilisz, István; Pataj, Zoltán et al. (2011) High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase. Chirality 23:549-56
Zhang, Xiaotong; Bao, Ye; Huang, Ke et al. (2010) Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases. Chirality 22:495-513
Sipos, Laszlo; Ilisz, Istvan; Pataj, Zoltan et al. (2010) High-performance liquid chromatographic enantioseparation of monoterpene-based 2-amino carboxylic acids on macrocyclic glycopeptide-based phases. J Chromatogr A 1217:6956-63
Lantz, Andrew W; Bisha, Bledar; Tong, Man-Yung et al. (2010) Rapid identification of Candida albicans in blood by combined capillary electrophoresis and fluorescence in situ hybridization. Electrophoresis 31:2849-53
Huang, Ke; Zhang, Xiaotong; Armstrong, Daniel W (2010) Ionic cyclodextrins in ionic liquid matrices as chiral stationary phases for gas chromatography. J Chromatogr A 1217:5261-73
Berkecz, Robert; Ilisz, Istvan; Benedek, Gabriella et al. (2009) High-performance liquid chromatographic enantioseparation of 2-aminomono- and dihydroxycyclopentanecarboxylic and 2-aminodihydroxycyclohexanecarboxylic acids on macrocyclic glycopeptide-based phases. J Chromatogr A 1216:927-32
Sun, Ping; Macdonnell, Frederick M; Armstrong, Daniel W (2009) Enantioselective Host-Guest Complexation of Ru(II) trisdiimine complexes using neutral and anionic derivatized cyclodextrins. Inorganica Chim Acta 362:3073-3078
Bao, Ye; Lantz, Andrew W; Crank, Jeffrey A et al. (2008) The use of cationic surfactants and ionic liquids in the detection of microbial contamination by capillary electrophoresis. Electrophoresis 29:2587-92
Pataj, Zoltan; Ilisz, Istvan; Berkecz, Robert et al. (2008) Comparison of performance of Chirobiotic T, T2 and TAG columns in the separation of beta2- and beta3-homoamino acids. J Sep Sci 31:3688-97
Wang, Chunlei; Armstrong, Daniel W; Chang, Chau-Dung (2008) Rapid baseline separation of enantiomers and a mesoform of all-trans-astaxanthin, 13-cis-astaxanthin, adonirubin, and adonixanthin in standards and commercial supplements. J Chromatogr A 1194:172-7

Showing the most recent 10 out of 89 publications