Biomimetic models of pyrroloquinoline quinone in a host-guest environment

ORGN 178

Andrew A Kennedy, andrewk@chem.gla.ac.uk1, Graeme Cooke, graemec@chem.gla.ac.uk1, and Stuart A. Macgregor, s.a.macgregor@hw.ac.uk2. (1) Department of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow, G12 8QQ, United Kingdom, (2) School of Engineering and Physical Sciences, Heriot-Watt University, William Perkin Building, Heriot-Watt University, Edinburgh, EH14 4AS, United Kingdom
Pyrroloquinoline Quinone (PQQ; 4,5-dioxo-4,5-dihydro-1H-prrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid) has received much attention as a novel coenzyme of various important oxidoreductases and dehydrogenases. PQQ has a unique o-quinone structure whereby the o-quinone active site is condensed by an electron withdrawing pyridine nucleus and an electron donating pyrrole ring. These fused substituent groups give PQQ an electronic character that differs to that of simple o-quinone systems. This study aims to synthesise two derivatives of PQQ, with different fused substituent groups in order to observe and quantify the effects these have on the reactivity of the cofactor and its ability to non-covalently bind to a suitable receptor. DFT molecular modelling calculations have also been carried out on the two accessible redox states of the system to further illustrate the electronic character and geometry of the cofactor when bound in a supramolecular environment.

 

Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007