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

Peptide / polymer conjugates nanotubes

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 Chem2011, 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.

 

 


For further information, please contact:

Professor Kate Jolliffe

Room 515

School of Chemistry

Eastern Avenue

University of Sydney NSW 2006

Phone: +61 2 9351 2297

Email: kate.jolliffe@sydney.edu.au