Molecular recognition has become a very important field of research in chemistry during the last decades. This<br />chemical phenomenon is responsible for all processes occurring in biology and asymmetric synthesis is based<br />upon the capability of molecules or substrates to recognise each other in a selective manner. In this thesis, the<br />design, preparation and evaluation of a series of new synthetic receptors has been described. The importance of<br />regioselectivity and stereoselectivity in molecular recognition has also been underlined with two different<br />biological examples.<br />The capability of host molecules, derived from (+)-tartaric acid, to accommodate various guests in a selective<br />manner was demonstrated using 1H-NMR spectroscopy (paper I). These host molecules, known as TADDOLs,<br />enantioselectively recognised the valuable chiral alcohols glycidol and menthol. Macromolecular receptors, i.e.<br />molecularly imprinted polymers (MIPs), were also prepared in order to catalyse the aldol reaction between either<br />(R)- or (S)-camphor and benzaldehyde (paper II). With the help of analytical methods, it was demonstrated that<br />the MIPs interacted in a selective manner with the enantiomers of camphor. Moreover, these MIPs enhanced<br />significantly the rate of the aldol condensation mentioned above.<br />Regarding biological systems, various regioisomeric analogues of benzoic acid have been tested as antifeedants<br />against the pine weevil Hylobius abietis (paper III and IV). The regioisomers studied displayed very different<br />antifeedant activities. The significance of stereoisomerism on pheromone function has been shown in the<br />preparation of lures for the control of the insect pest Argyrotaenia sphaleropa (paper V). It was demonstrated that<br />male leafrollers could be caught by a lure containing components of the female sex pheromone gland.
| Identifer | oai:union.ndltd.org:CCSD/oai:tel.archives-ouvertes.fr:tel-00080096 |
| Date | 02 March 2006 |
| Creators | Legrand, Sacha |
| Source Sets | CCSD theses-EN-ligne, France |
| Language | English |
| Detected Language | English |
| Type | PhD thesis |
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