Abstract

The objective of this project is to develop fluorescent sensors for the enantioselective recognition of chiral organic compounds and drug molecules. These sensors will be constructed by using optically active binaphthyl-based chiral molecules and dendrimers. As an application of these enantioselective fluorescent sensors, a combinatorial screening of the Schiff base-Lewis acid catalysts for the asymmetric reaction of aldehydes with TMSCN is proposed. With the use of the proposed enantioselective fluorescent sensors, it is expected to quickly identify the highly enantioselective catalysts in the combinatorial matrixes with only one or two fluorescence measurements. The enantioselective fluorescent sensors will also be used for the high through-put search of highly enantioselective, easily available, and environmentally benign catalysts for several other asymmetric reactions. The utility of the sensors will be expanded by preparing their Lewis acid complexes. The good coordination and chiral recognition ability of the Lewis acid complexes may allow the enantioselective fluorescent recognition of other chiral organic molecules such as amines, amino alcohols. aldehydes, ketones, and heterocycles.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
2R01GM058454-03A1
Application #
6382601
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
1999-01-01
Project End
2005-06-30
Budget Start
2001-07-01
Budget End
2002-06-30
Support Year
3
Fiscal Year
2001
Total Cost
$215,734
Indirect Cost

  Institution

Name
University of Virginia
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
001910777
City
Charlottesville
State
VA
Country
United States
Zip Code
22904

  Publications

Wang, Qin; Chen, Xi; Tao, Lan et al. (2007) Enantioselective fluorescent recognition of amino alcohols by a chiral tetrahydroxyl 1,1'-binaphthyl compound. J Org Chem 72:97-101
Wang, Qin; Chen, Shan-Yong; Yu, Xiao-Qi et al. (2007) 1,1'-Binaphthyl Ligands with Bulky 3,3'-Tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes. Tetrahedron 63:4422-4428
Li, Zi-Bo; Liu, Tian-Dong; Pu, Lin (2007) Chiral macrocycle-catalyzed highly enantioselective phenylacetylene addition to aliphatic and vinyl aldehydes. J Org Chem 72:4340-3
Li, Zi-Bo; Lin, Jing; Sabat, Michal et al. (2007) Enantioselective fluorescent recognition of chiral acids by cyclohexane-1,2-diamine-based bisbinaphthyl molecules. J Org Chem 72:4905-16
Rajaram, Amaresh R; Pu, Lin (2006) Regiospecific hydration of gamma-hydroxy-alpha,beta-acetylenic esters: a novel asymmetric synthesis of tetronic acids. Org Lett 8:2019-21
Hyacinth, Marilise; Chruszcz, Maksymilian; Lee, Ki Sung et al. (2006) Supramolecular assemblies of chiral propargylic alcohols. Angew Chem Int Ed Engl 45:5358-60
Qin, Ying-Chuan; Liu, Lan; Pu, Lin (2005) On-step synthesis of a bifunctional BINOL ligand for the highly enantioselective cyanation of aliphatic aldehydes. Org Lett 7:2381-3
Li, Zi-Bo; Lin, Jing; Qin, Ying-Chuan et al. (2005) Enantioselective fluorescent recognition of a soluble ""supported"" chiral acid: toward a new method for chiral catalyst screening. Org Lett 7:3441-4
Pu, Lin (2004) Fluorescence of organic molecules in chiral recognition. Chem Rev 104:1687-716
Li, Zi-Bo; Lin, Jing; Zhang, Hui-Chang et al. (2004) Macrocyclic bisbinaphthyl fluorophores and their acyclic analogues: signal amplification and chiral recognition. J Org Chem 69:6284-93

Showing the most recent 10 out of 19 publications