Cyclodextrin Assisted Enantiomeric Recognition of Amino Acid Imides and Toward Synthesis of Dolabellane Diterpenoid B

There is a strong market demand for enantiomerically pure drugs. One solution to this problem is to develop a simple methodology for transferring synthetically designed racemic drugs into optically pure ones. Many synthetic drugs are by nature amides, therefore, amino acid based models for transformation of racemates into optically pure compounds were selected for this study. Formation of self-assembly molecular aggregates of properly modified amino acids was observed with and without the presence of cyclodextrins. Cyclodextrin assisted formation of polymer-like self-assemblies and enantiomeric resolution of these amino acids were studied using 1D and 2D NMR spectroscopy, EleacroSpray Ionization Mass Spectroscopy (ESIMS), Matrix- Assisted Laser Desorption Ionization Time-of-Flight Mass Spectroscopy (MALDI-TOF-MS). The role of p-p stacking interaction between aromatic moieties in enantiomeric resolution was demonstrated by calculating association constants of this host-guest system. Dolabellane diterpenoids share the unique feature of a trans-bicyclo[9.3.0]tetradecane and most of them express antimicrobial, antitumor and antiviral activities. They are primarily obtained from marine resources. Dolabellane diterpenoid B was isolated from the Okinawan soft coral of the genus Clavularia by Iguchi and co-workers. Current efforts toward the synthesis of dolabellane diterpenoid B is discussed along with the plans for completion of its synthesis.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Year

2005

Author dc:creator

• Patel, Pareshkumar

Contributors dc:contributor

• Jursic, Branko
• Wang, Guijun
• Trudell, Mark

• Enantiomeric Recognition

Repository record dc:identifier

https://scholarworks.uno.edu/td/307

OAI identifier oai:identifier

oai:scholarworks.uno.edu:td-1340