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A team of chemists at UOW is using gold to create new molecules that could be used in pharmaceuticals.

A love of fireworks ignited an interest in chemistry for UOW Senior Lecturer Chris Hyland.

Born and raised in the UK, Dr Hyland spent his childhood taking things apart, exploring and making his own chemistry sets.

“I really liked fireworks,” Dr Hyland laughs.

“I got my first chemistry set when I was eight years old and that was probably my first inspiration – I was hooked on mixing solutions in test tubes and figuring out what would happen.” He then went on to study chemistry and medicinal chemistry at one of London’s leading chemistry schools.

While completing a PhD at Imperial College London, a textbook on metal catalysis by Professor Louis Hegedus intrigued Dr Hyland.

“I became fascinated by the ability of these metals to transform simple molecules into highly complex structures by what can almost be described as molecular gymnastics,” he says.

Inspired by this research area, Dr Hyland went on to work with the author in the US at Colorado State University, where he developed new ways to make nucleoside analogues using metal catalysts.

His foray as an independent academic began in California, where Dr Hyland worked on programs designed to involve minority and underrepresented students in the STEM field. There he struck on the idea of combining metal catalysts with highly strained molecules to unlock new chemical reactions.

“Many of these molecules have triangular shapes which causes their bonds have unfavourable angles, which is the main reason for them being strained or highly reactive,” he explains.

“Think of these strained molecules as a jack in the box, with the gold catalyst acting as the trigger to release the energy stored in the system resulting in the formation of a new biologically important chemical structure.”

A goldmine of reactions

A synthetic chemist, Dr Hyland uses gold to create new chemical reactions.

“The particular area we focus on is catalysts; using metal to do reactions that have never been done before,” he says. “Gold is highly reactive when in a certain oxidation state, allowing new chemical reactions to be discovered.

“As an element it’s really stable, but when you oxidise the metal it becomes very reactive.”

Using gold as the key catalyst, Dr Hyland hopes to design reactions that could be used to make new chemical structures in pharmaceuticals – without having a negative impact on the environment.

“We’ve found that gold has a number of key advantages; reaction times are short which saves on energy costs, and gold is non-toxic in comparison to many other chemical reagents,” he says.

“One of the reactions we developed occurs in a few seconds, whereas with other metals the reaction might need to be heated at high temperatures for a couple of days. Catalysts can help us develop a new toolkit for molecule synthesis, in a very energy efficient manner.

Gold has similar properties to other metals, such as mercury, but doesn’t have toxicity and won’t send you mad as a hatter.

Dr Chris Hyland

The use of ‘spring-loaded’ or ‘strained’ triangular molecules in concert with gold catalysts could be the key to making new structures that could one day be turned into medicines. Gold seems to be ideally matched to temporarily binding to these strained molecules in a reaction, kicking off a cascade of bond forming and bond breaking processes to produce a completely new molecule.

“Gold facilitates the journey but doesn’t end up in the final product, which is crucial to our research.” That means that while gold is relatively expensive, it can be used in very small quantities and recovered at the end of the reaction for re-use in another process.

Dr Chris Hyland and Melanie Drew. Photo: Paul Jones

Heterocycling all the way to Germany

In late 2016 Dr Hyland was announced as the successful recipient of grant funding under a scheme that fosters and encourages collaboration between Australian and German universities and research institutes.

The Australia-Germany Joint Research Cooperation Scheme is a joint initiative of Universities Australia and the German Academic Exchange Service (DAAD), Germany’s national agency for the support of international academic cooperation.

At the time of the announcement, Universities Australia Chief Executive Belinda Robinson said Germany was consistently ranked as the third most important country in terms of research collaboration for Australian universities.

“Germany is a world leader in innovation and research. This funding announcement will mean Australia can build even stronger ties with a country that is known as a research powerhouse and build our own research capacity in return,” Ms Robinson said.

“These projects are laying the ground work for our future large-scale collaborations, helping both nations to reap the economic and societal benefits of sharing cutting-edge research knowledge and practice.”

Led by Dr Hyland, the UOW expertise in strained molecule reactivity will combine with German expertise in gold catalysis to prepare a range of molecules known as heterocycles. These molecules feature in a vast array of medicines and materials.

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Under the research grant, PhD student Melanie Drew will travel to Germany later this year to work alongside the world leader in gold catalysed reactions, Professor Stephen Hashmi, at Heidelberg University.

Born and bred in the countryside on NSW’s southern border, Melanie describes her family as “very science-oriented”, with a pharmacist for a sister and an engineer and radiographer for brothers.

“Math and science were always pushed from when we were little,” she says. “My mum always liked maths and dad was an industrial arts teacher.”

Melanie found her passion for organic chemistry during her second year of undergraduate study at UOW.

“My motivation to go into the area was to help people – it becomes more indirect doing method reactions but you’re still helping people at the same time,” she says.

“I’d researched medicine and pharmacy and decided that chemistry was where I wanted to be.

“I like to think about the fundamentals and how stuff works, rather than what the drugs do, in my current work we’re making molecules that can be turned into useful drugs.”

As an undergraduate student, Melanie appeared on the UOW Faculty of Science Dean’s Merit List every year from 2011-2014 and received the University Medal for the Faculty of Science, Medicine and Health in 2014. She received the Leon Kane-Maguire Student Prize for the highest weighted average mark for Chemistry and/or Nanotechnology across all years of the degree in 2015, the Royal Australian Chemical Institute (RACI) Student Prize for outstanding performance in undergraduate chemistry subject in 2013, the Peter Beckmann Memorial Prize for best academic record in third year chemistry in 2013 and the G.W Daniels Memorial Prize for second Year Chemistry for best academic record in second year chemistry in 2012.

With her husband by her side, Melanie will spend the next six months at Heidelberg University focusing on triangular shapes that feature in several biologically active molecules.

“We know that several anti-fungals have these triangular shapes in them,” she says.

Because the body doesn’t know how to metabolise them, they stay longer in the body. It has implications for anti-bacterial, anti-cancer and anti-malarial drugs.

Melanie Drew

As for her travel partner, Melanie says he couldn’t be happier about the move to Germany.

“He’s an engineer, so he’ll be right at home with German efficiency and German cars,” she laughs.

A toolbox of reactions

Through international collaboration, Dr Hyland and his team hope to learn more about biological systems and fulfill the end-goal of making key pharmaceutical building blocks.

“The impact is potentially higher than making just one reaction,” Dr Hyland says.

“When you develop a new reaction the possibility is that it can be used in multiple pharmaceuticals.”

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