About

This is the website of Professor Andrea Robinson’s chemistry group at Monash University, Melbourne, Australia.

Our research uses catalysis to generate target molecules and to solve problems of biological significance. Some of the group are interested in organometallic synthesis and the exploration of catalytic cycles. Through developing new catalysts and understanding molecular processes we can advance capability and tackle the synthesis of complex molecular architecture. Our interest in organic chemistry extends from small molecules to large peptides and polymers of medicinal and industrial value. We are interested in generating sustainable and efficient alternatives to current processes and strive to find answers to the unknown.

If you are interested in learning more about our group or chemistry please contact me.


 

DISULFIDE REPLACEMENT CHEMISTRY

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Cystine bridges are common structural motifs in naturally occurring cyclic peptides. Using tandem catalytic sequences and specially designed non-proteinaceous amino acids, we have developed a way to control the formation of up to five dicarba-bridges. We have several projects examining the preparation of carbocyclic derivatives of naturally occurring cystine containing molecules, including conotoxins (see CtxIMI below), biologically active peptide neurotoxins and insulin super-family molecules.

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Selective alkene and alkyne metathesis routes have also been explored as a route to complex biologically active toxins. We have recently developed a new way of combining alkene and alkyne metathesis to achieve regioselective C-C bond formation.

 


ALTMET POLYMERISATION

We are also interested in synthetic vaccines for the prevention of a wide range of diseases. We have used a regioselective metathesis reaction to construct antifreeze agents, bioelastomers and a synthetic vaccine against enteropathogenic bacteria, which are responsible for the vast majority of diarrhoeal diseases in the world and millions of deaths each year. The vaccine research is performed in collaboration with Professor David Jackson at the University of Melbourne and our bioelastomer work is conducted with Dr Chris Elvin (CSIRO).

 


NC CYCLIC PEPTIDES

The synthesis of cyclic peptides is a difficult exercise and several research groups have tried to address this problem. Our recently developed strategy relies on the installation of a temporary alkene tether to bring the C and N peptide termini within close proximity, enhancing amide coupling.  The alkene tether is then removed by treatment with 2-butene under metathesis conditions. This methodology has been successfully applied to the synthesis of several Mahafacyclin analogues, an antimalarial cyclic peptide, resulting in improved peptide cyclisation yields when compared to the cyclisation efficiency of the linear peptide.

 


NATURAL PRODUCTS

Our group has a long standing interest in catalysis, particularly when it is applied to asymmetric synthesis and peptidomimetics. We are interested in the synthesis of new ligands and catalysts, tandem and asymmetric catalysis and the application of catalysis to biological targets, i.e. β-lactam antibiotics, β-lactamase inhibitors, taxane anticancer compounds and natural products, including spirocyclic alkaloids. We have developed asymmetric catalytic routes to β-amino acids and pseudoproline analogues. We have many active projects in this area.


RENEWABLES CHEMISTRY

The recent rises in the cost of petroleum feedstocks coupled with diminishing world reserves have prompted a revival of interest in the use of renewable natural oils. Research efforts within the Robinson/Jackson group, led by Jim Patel (Postdoc 2002-2006), identified that butenolysis is superior to ethenolysis in regard to metathesis catalyst turnover, enabling efficient formation of valuable fine chemicals from natural oil feedstocks such as canola and sunflower oil.  We have also demonstrated that this process is compatible with the production of high value terminal oxygenates using a tandem sequence of cross-metathesis/palladium catalysed isomerization/methoxycarbonylation. We have several on-going projects in this area.

 

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