organic synthesis and supramolecular chemistry
My research focuses on the design, synthesis and investigation of the properties of molecules with specific functions. It spans a number of areas including (i) the development of new synthetic methods; (ii) application of these methods to the synthesis of both natural products and novel functional molecules and (iii) the synthesis and investigation of small molecule mimics of Nature’s molecular receptors and enzymes (supramolecular chemistry). All projects involve synthesis, with some also involving physical and/or biological techniques.
Project 1
Supramolecular peptides: Anion sensors and transporters
Anions play many roles in areas as diverse as biology, medicine, catalysis and the environment. Artificial anion receptors capable of sensing or transport across membranes have numerous applications, particularly in the area of biomedicine. However, the development of anion receptors that operate with high selectivity and affinity under physiological conditions remains a significant challenge. Modified peptides provide versatile scaffolds for the synthesis of such sensors and transporters. Projects are available in developing the synthesis of such molecular scaffolds and in the synthesis and evaluation of novel anion receptors (see e.g. Chem. Commun., 2011, 47, 463). These projects would suit students with an interest in either synthesis or techniques including the use of NMR, mass spec, UV-vis and fluorescence for the study of molecular interactions.
Project 2
Improving the synthesis of cyclic peptides
Cyclic peptides are a class of interesting molecules with a variety of biological activities. However, the synthesis of many of these deceptively simple-looking molecules is often challenging. We have recently developed a method to improve the synthesis of small cyclic peptides (Org. Lett., 2010, 12, 3136). Projects are available in applying this method to the synthesis of natural products and also in the synthesis of novel cyclic peptides with a variety of potential applications. Projects will suit students with a strong interest in organic synthesis.
Project 3
Novel antifungal compounds
Invasive fungal infections (mycoses) are becoming increasingly implicated as a cause of serious and fatal diseases. Current drugs are limited in safety and/or efficacy and resistant fungi are an emerging problem. New antifungal drugs with novel modes of action are urgently needed. With collaborators from Westmead hospital, we have identified several classes of compound that have strong antifungal activity. This project will involve the design, synthesis and biological assays of new antifungal compounds (e.g. LI-F04a; Org. Lett., 2010, 12, 3394). It will suit students with interests in both organic synthesis and medicinal chemistry.
Project 4
Peptide / polymer conjugates nanotubes (with Professor Seb Perrier)
Hollow nanotubular structures are present in many natural and artificial systems, for instance transmembrane channel proteins and carbon nanotubes. We recently developed a novel approach to engineer organic (“soft”) nanotubes by conjugating well-controlled polymeric chains to cyclic peptides (Polym Chem, 2011, 2, 1956). By assembling via β-sheet-like antiparallel hydrogen-bonding interactions, the cyclic peptides direct the assembly of the polymeric chains into nanotubes. The aim of this project is to further develop these nanotubes into transmembrane channels for cells and test them as ion-pumps and as antibiotics.
I am away until January 2013 so to discuss Honours projects please send me an email.
For further information, please contact:
Room 545
School of Chemistry
Eastern Avenue
University of Sydney NSW 2006
Phone: +61 2 9351 2297
Email: kate.jolliffe@sydney.edu.au