Functional Molecular Systems by Template-Guided-Cl.. (Click-Fun)
Functional Molecular Systems by Template-Guided-Click Assembly
Start date: Sep 3, 2007,
End date: Sep 2, 2009
One of the most challenging tasks in current chemical research is the creation of molecular systems with defined activities, such as catalysts or target specific molecular recognition materials for separation and sensing. Current state of art in this field utilizes primarily screening and combinatorial synthesis whereas de novo design is using with the limited success rate. This project proposes an alternative, innovative approach to create the functional molecules such as artificial receptors and catalysts by combination of template-guided click chemistry assembling (TGCA). Specifically, pair of highly functionalized fragments: an azide and an alkyne is assembling on the template. For receptors the desired target molecule is used as the template whereas the transition state analogue is used for the catalyst templating. Only best combination of substrate pair due the proximity of azide and alkyne functions may undergoes click fusion (Huisgen cycloadditon, up-to-date most powerfull click chemistry tool). The resultant triazole linked hybrids accumulates the interaction sites of single partners thus should effectively recognized the template (receptor) or should possess the desired catalytic activity (analogy to catalytic antibodies). The presented idea will be utilized for the construction of receptors for the important anticancer drug taxole and its precursor as well for artificial hydrolytic enzymes. The coupling pairs of azides and acetylenes will be iteratively selected from aminoacids, di- and tripeptides and specific compounds which are known to have high affinity to desired templates, thus increasing the probability of success. This project may delivery a new approach for production of new functional molecules and the resultant receptors and catalysts may find practical application in manufacturing and analytics of taxane family (receptor, purification) and organic synthesis (artificial enzymes).
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