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ChemNEWS

ISSUE 20

2012

Newsletter of The University of Sydney School of ChemistryChemNEWSSCHOOL OF CHEMISTRYFACULTY OF

SCIENCE

BORON IS THE NEW CARBON BY ASSOCIATE PROFESSOR LOU RENDINA

Boron and gadolinium are two elements that are central to our research program but why the interest in these two, quite disparate, elements? The answer is simple. Their chemistry is not only fascinating but each element offers its own distinct challenges and unique characteristics with potential application in medicine. By the use of these elements, I believe a real opportunity exists for significant paradigm shifts in the area of drug development. In this brief article, I will focus on only one of these elements and the diverse roles it can play in medicine.

Boron, in the form of boric acid, has been used as a mild antiseptic and eye wash since the 18th century. However, the use of boron in drug design is only a recent phenomenon, with the pharmaceutical industry and an increasing number of medicinal chemistry researchers now substituting boron for its neighbour carbon in numerous classes of drug molecules. Safety and synthetic concerns have been overcome by significant advancements in the area of boron chemistry and the abundance of safety data for the element. In the area of drug design, boron molecules may be used to target biological receptors that appear to be unaffected by organic frameworks, a property that may be exploited in areas such as bacterial drug resistance, for example. Recently, some potent boron-containing drugs have either become commercialised or have entered clinical trials. Velcade® (bortezomib) was the first clinically-assessed and commercially approved boron-containing drug for the treatment of newly-diagnosed multiple myeloma. In late 2011, Anacor Pharmaceuticals completed enrolment in two identical Phase 3 clinical trials for the boron-containing drug AN2690 (Tavaborole®) used to treat onychomychosis, a fungal infection of the nail and nail bed. Several other boron drugs are also at the advanced stages of clinical development. These drugs contain boron-based functional groups including diazaborines, boronic acids and esters, and

benzoxaboroles. Boron clusters are another class of molecules showing great potential in the area of drug design. Certain polyhedral boranes such as the carboranes (dicarba-closo-dodecaboranes) are kinetically stable to hydrolysis and can offer many exciting possibilities in medicinal chemistry. It is the three-dimensional delocalisation (or “pseudo-aromaticity”) of the s-framework electrons in these unique entities that largely accounts for their remarkably robust properties.

The closo-carborane cluster (Figure 1) is a neutral, hydrophobic analogue of the hydrophilic, icosahedral ion closo-[B

12H

12]2-, the largest cluster

belonging to the family of polyhedral boranes with the general formula closo-[B

nH

n]2- (where n = 6 - 12). The

syntheses of closo-carboranes were reported in the early 1960s. Notably, these unusual boron compounds were discovered in the late 1950s but were not declassified until 1962. At the time, the US Government was supporting programs to develop alternative high-energy fuels for rockets and jet aircraft and it was these initiatives that led to the discovery of carboranes which, along with their boron-rich precursors (such as decaborane), were prepared in multi-tonne quantities.

The experimental cancer treatment known as boron neutron capture therapy (BNCT) paved the way for the use of boron clusters in medicine, particularly in the treatment of glioblastoma multiforme (GBM), an

Figure 1: The molecular structure of the most common carborane, closo-1,2-carborane. The “closo” descriptor refers to a complete icosahedron with no missing vertices. There are three known isomers of this molecule differing only in the relative positions of the two carbon atoms within the icosahedron. Boron atoms are coloured gold, carbon atoms are grey, and hydrogen atoms are white.

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A/PROF. LOU RENDINA

Lou’s interest in chemistry was sparked at a very young age with the gift of an

oversized chemistry set from his grandfather, well before OH&S laws were enacted. The absence of any tangible excitement associated with growing up in Canberra during the 1970s meant that he kept himself busy by performing untested chemical reactions in pursuit of the world’s best rocket fuel, investigations that one time led to the explosive spattering of his lounge room ceiling with an indelible bright-orange dye. He put this awesome reaction to good use by entering a fully-functional model volcano in a Year 7 science competition that won him an award for the “most imaginative” science project. Lou then spent almost a year working on his most ambitious project − a one metre high, hybrid-fuelled rocket constructed from PVC piping. But his attempts failed badly when the rocket tipped over soon after ignition and then slammed into his family garage door with explosive vigour, much to the delight of his brother and onlookers. His father calmly saw through these unfortunate incidents (probably relieved that the rocket or orange dye never caused any

injury) and so he built Lou a secluded laboratory in the newly-repaired family garage, equipped with modest glassware and chemicals provided by his supportive high-school science teachers (including a cricket-ball sized lump of potassium metal − but that’s another story), a Bunsen burner, safety shower, and fire extinguisher. In Year 10, Lou was awarded a scholarship to attend the Canberra School of Music but he always knew that chemistry was his true calling and he later took up an offer from the Australian National University to study Science. Lou received his BSc(Hons I) and PhD degrees under the supervision of Professor John A. Broomhead, a former PhD student of the bioinorganic chemistry pioneer, Professor Francis P. Dwyer. After witnessing a seminar presented by Professor Martin A. Bennett, FRS, Australia’s foremost organometallic chemist, Lou wanted to try his hand at a different area of chemistry and he convinced Martin that a bioinorganic chemist was exactly the sort of person who should be working on the reaction mechanisms of organoplatinum-hydroxo complexes with unsaturated hydrocarbons. For some odd reason, Martin accepted the challenge and offered Lou a project he’d never forget. Lou was then awarded a NSERC Canada International Fellowship and he journeyed to Canada to undertake fundamental research concerning the oxidative addition reaction with the renowned organometallic chemist

Professor Richard J. Puddephatt, FRS. The bitter cold of two Canadian winters finally took its toll on Lou and he returned to Australia and took up his first academic position at the Department of Chemistry, The University of Adelaide. In late 2003, he moved to the University of Sydney.

Lou is the recipient of two prestigious national awards from the Royal Australian Chemical Institute (RACI) for his seminal contributions to the areas of Medicinal Chemistry (RACI Biota Medal for Medicinal Chemistry) and Organometallic Chemistry (RACI Organometallic Chemistry Award), the only individual to have ever received both awards. He has also been elected as a Fellow of the RACI (FRACI, C. Chem.) and a Fellow of the Royal Society of Chemistry, UK (FRSC). His current research interests lie in the area of bioinorganic medicinal chemistry, in particular the development of new boron and gadolinium agents for neutron capture therapy and in the use of boron clusters as pharmacophores in medicinal chemistry.

In his rare spare time, Lou enjoys watching arthouse films, especially those directed by David Lynch, pursuing his life-long hobbies of photography and amateur astronomy, reading sci-fi novels, grappling with the literary works of Tolkien’s legendarium, and dining at Inner West eateries whilst discussing the latest happenings in clinical research with his wife, Dr Daniela Caiazza.

aggressive and intractable malignant brain tumour. BNCT is normally referred to as a “binary therapy” as it makes use of two key components that can be manipulated independently. One of the components is the non-radioactive 10B isotope which possesses a large, effective neutron capture cross-section (3838 barns). It has the unusual capacity to capture low-energy thermal neutrons (the second component) and undergo a fission process that results in the formation of high linear energy transfer (LET) particles (alpha particles and Li ions) and a tremendous amount of kinetic energy (~2.4 MeV). Importantly, the high LET particles possess very short path-lengths (< 10 μm) and so their cytotoxic effect is largely confined to the cell in which the 10B agent is located. Numerous clinical studies have clearly demonstrated the safety of BNCT in the treatment of GBM, and its efficacy is at least comparable to the best of conventional radiotherapy. BNCT is the frontline treatment for GBM in Japan, and it usually follows surgical (“debulking”) procedures as a way of destroying any remaining tumour cells. Boron clusters possess several important features that make them amenable as BNCT agents and, indeed, one polyhedral borane known

as borocaptate ion (BSH, [B12

H11SH]2–) is used clinically

despite its poor tumour selectivity. Notably, boron clusters are boron-rich and so the probability of a neutron capture event within tumour cells is dramatically increased when compared to similar types of molecules possessing a low boron content, e.g. boronic acids. In our own research program, we have discovered several new classes of potential BNCT agents based upon carboranes,

Figure 2: The molecular structure of the most common nido-carborane, nido-7,8-carborane. The “nido” (“nest like”) descriptor refers to an incomplete icosahedron with one missing vertex. Boron atoms are coloured gold, carbon atoms are grey, and hydrogen atoms are white.

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THIS TIME

BY PROFESSOR GREG WARR

HEAD OF SCHOOL

That’s Hervé This time, during which we learned much about the benefits of eggs cooked at 68 °C, and a foamy meringue (also mainly egg) cooked in N

2(l) at -196 °C.

Our Molecular Gastronomy evening, held late last October, was a great success. It not only showcased molecular gastronomy (or molecular cuisine, depending on whether your making, eating, or studying it), but also drew the audience’s attention to a large number of ‘good’ chemicals. We all know that Chemicals are Good for You* but somehow it seems even more true when you can literally taste it. Professor This and Chef Martin Benn were a terrific double act, and our Teaching Fellows did a great job as petit fours in the Quadrangle engaging all our guests with up close demonstrations of food-related chemistry.

The School was also a focus during the 2012 Sydney Festival, hosting the Vision in Motion installation by artist Narelle Jubelin. This exhibit in the Lecture Theatre foyers married the architecture of the school with its functions of teaching and research, and incorporated some of our wireframe molecular models alongside Narelle’s remarkable petit point renderings of buildings of diverse architectural styles, and a photoessay led by Jackie Redgate. Although the display is over, our models will remain on at least semi-permanent display. Look up next time you’re in the foyer.

This time is also a time of change in the School of Chemistry, with many new faces. Some, including our latest addition to the academic staff ranks, Dr Liz New, are profiled in this issue. We welcome Liz and congratulate her on her ARC DECRA. There has also been a lot of turnover among the administrative and technical staff over the past year or so, including permanent arrivals and departures as well as maternity leave and secondment replacements. As much as we miss those who have left, it’s been a real pleasure to welcome new staff, to see the new skills and energy that they bring, and to see how well they have all fit into and enhanced the operations of the School across many fronts. These staff members fill critical operational roles, so when we have change, it’s reassuring to see that we’re heading in the right direction.

* The title of Peter Rutledge’s 2009 RACI Nyholm Youth Lecture

e.g. platinum-amine complexes and DNA metallointercalators

that can avidly bind to DNA within tumour cells, phosphonium

salts that can selectively target tumour-cell mitochondria, and

selective agents that can enter hypoxic regions of tumours.

Boron clusters also offer other exciting possibilities in the

treatment of disease. The closo-carboranes represent a

unique type of pharmacophore which can bind to protein

sites by hydrophobic interactions that exploit the largely non-

polar character of B-H bonds. The use of closo-carboranes

in medicinal chemistry marries the properties of polycyclic

cage skeletons such as those of adamantane with the unique

characteristics of boron to offer a unique and versatile

pharmacophore in the field of drug discovery. Carboranes have

given researchers the ability to synthesise molecules with highly

specific shape and charge distributions, and a considerable

amount of research in recent years has shown that some

carborane-containing bioactive molecules may prove to be

superior to some of their organic counterparts. Furthermore,

by means of a simple and selective deboronation reaction, one

can completely transform a hydrophobic closo-carborane into

a hydrophilic, anionic cluster, a species that is referred to as a

nido-carborane (Figure 2). In collaboration with the Kassiou

group, we are currently evaluating the application of these

unique pharmacophores in the treatment of CNS diseases,

e.g. Alzheimer’s disease and depression, and also as potent

inhibitors of the over-expressed translocator protein (TSPO)

that is usually associated with the growth of aggressive

malignant tumours such as those of the brain and breast.

Preliminary animal studies demonstrate the potential of these

unique molecules in the treatment of certain diseases and we

are actively exploring new drug targets.

In conclusion, with the exception of platinum anti-cancer

drugs, medicinal chemistry over the past century has almost

exclusively made use of organic frameworks in the development

of new drugs but their so-called “chemical space” appears

to be somewhat restricted when one considers the many

challenges of drug design. It is clear that the use of molecular

frameworks in medicinal chemistry (and, indeed, organic

synthesis as a whole) in recent decades has largely followed a

distinctive “power law” distribution, i.e. only a limited number

of molecular frameworks are utilised by chemists over and

over again, predominately due to their commercial availability,

lower costs over alternatives, established chemistry, and the

wide-spread adoption of C-C bond coupling reactions such

as the Suzuki reaction. When one also includes other aspects

of “druglikeness” into the analysis (for example, entities that

satisfy Lapinsky’s “rule of 5”), the number of medicinally-useful

molecular frameworks becomes even more restricted. Indeed,

a lack of structural diversity among lead compounds has been

cited by several authors as a potential bottleneck in the drug

discovery process. The unique chemistry of boron compared

to its adjacent neighbour carbon offers great promise in the

search for novel drug leads with unique properties for the

treatment of disease, and pharmaceutical companies are now

beginning to take notice of its great potential. Perhaps boron

really is the new carbon!

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GASTRONOMICAL DELIGHTSBY DR MAT TODD

We are what we eat. Or maybe we eat what we are. Chemistry and cooking are closely related. A deeper understanding of food’s nature lets us bring out the most delicate tastes, and the science behind even the simplest dish can have great complexity. For the International Year of Chemistry, the University hosted a showcase of Molecular Gastronomy with one of the founders of the discipline, Professor Hervé This, and an award-winning Sydney chef, Martin Benn. With the help of many members of the School and Faculty, the RACI, and some in-event help from the Vice Chancellor and the Dean of Science, we showed that great cuisine is a mixture of science, art and …

L-R: Hervé This explains molecular gastronomy as Martin Benn (left) and Adam Spencer look on

To view all photos from the night please visit Chemistry FacebookPhotos courtesy of Jayne Ion (b-side.com.au)

A couple of years ago I was talking with the Faculty of Science marketing team about putting on an event to demonstrate how important Chemistry is to our daily lives. Our most direct relationship with chemicals (or as they are sometimes called, Food) is when we eat them. Perhaps we had been watching too much Iron Chef, but the outcome of the conversation was that we proposed to put on live demonstrations of how chemistry underpins so much of what we taste, smell and cook. We didn’t want a cooking show, but rather something based firmly in science. By chance I had recently heard that the famous French scientist and “Molecular Gastronomist” Professor Hervé This (of the National Research Institute

known as AgroParisTech) was writing a blog, and regularly formulating new recipes with the chef Pierre Gagnaire; together they applied scientific methods to understand the cooking process in great detail. I contacted Hervé and he agreed to come about a year hence. He was one of the founding fathers of molecular gastronomy, which has achieved high public awareness through its use by chefs such as Heston Blumenthal of the Fat Duck, and Ferran Adria of El Bulli.

Hervé was trained as a physical chemist. He names his creations after famous scientists: an egg white/oil emulsion cooked in a microwave is a “Gibbs”. Hervé does not, however, own

or run a restaurant. To complete the event the Faculty Marketing Team, led by Kristl Mauropoulos, invited an award-winning Sydney Chef, Martin Benn of Sepia Restaurant, to co-present a lecture and highlight recent developments from his kitchen. He had developed a recipe called Japanese Stones, so called because it appeared as a set of beautiful pebbles resting on moss. From the picture, I wondered where the edible part might be, before realising the entire thing was a dessert.

During the show Hervé demonstrated a number of “classic” aspects of Molecular Gastronomy. From my vantage point I had an excellent view of the streams of “smoke”

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Martin Benn’s Japanese stones

Mat Todd (USYD), Hervé This and Max Crossley (USYD)

Gerard O’Connor (USYD)The Great Hall, The University of Sydney Teaching Fellow, Derrick Roberts, in action in the quadrangle

emerging from the Vice Chancellor and Dean following their eating a liquid nitrogen-cooked delicacy. The exuberant professor was perfectly counterbalanced by the laconic chef who had prepared a mesmerising video of the craft involved in preparing the Japanese Stones. As if by magic each person in the Great Hall was presented with a stone to taste (which was delicious). The evening, improvised and fast-moving, was skilfully hosted by Adam Spencer.

Hervé was visiting Sydney for five days with his wife Pascale, who is an endocrinologist and who gave a talk at Genea (Sydney IVF) in the city. Hervé found time to demonstrate the Gibbs and other things to reporters with the help of our very own students Katrina Badiola, Cyril Tang, Lara Malins and John Moraes (featured in the Herald at http://bit.ly/nfaDMF). He gave us a more detailed description of a General Formalism for Sauces, in which he had reduced all textbook (cookbook) examples to a handful of types, and by doing so was able to predict new sauces yet to be made. He gave an interactive lecture to the Talented Student Program cohort that included a shockingly good demonstration of how to “unboil” an egg with sodium borohydride.

Hervé is a wonderful ambassador for the role of precision and science in the preparation of new dishes. His progression of ideas starts with the need to understand what is in food – i.e. how best to handle dishes, how best to modify them, how we can use this knowledge to discover new ways of cooking. He led us through to

the logical extreme of a new field he

has invented called “Note-by-Note”

cuisine, in which he is making (and

has served to people) dishes created

entirely out of pure chemicals, of the

kinds that we use in the lab. However,

Hervé’s most important message

in his main lecture in the Great Hall

was left to the end. After leading us

through the reductionism of Note-

by-Note cuisine, he made it clear that

Chemistry and Cooking are not the

same. What was the main difference?

He saved it for the final word - Love!

Sincere thanks go to all the Teaching

Fellows who so ably demonstrated

how basic science in involved in so

many aspects of taste and cooking,

and to A/Prof Adam Bridgeman for

helping to organise that part of the

evening. Behind the scenes there was

a great deal of logistical support from

the Service Room staff, particularly

Marjan Ashna and Carlo Piscicelli.

Thanks also to the RACI for teaching

us all how to make sherbert, and lastly

to Kristl and the Faculty Marketing

Team, without whom none of this

would have happened. The Japanese stones are served in the Great Hall

Chemical demonstrations in the QuadrangleL-R: Martin Benn, Hervé This and Adam Spencer

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Liz joined the School of Chemistry in January 2012, almost ten years after she first arrived as an undergraduate student. She received her BSc (Adv, Hons) in 2005 and her MSc in 2007, working with Professor Trevor Hambley on fluorescent analogues of cisplatin. She then moved to the UK to undertake a PhD at Durham University with Professor David Parker, studying luminescent lanthanide complexes for use as cellular probes. In this work, funded by a Commonwealth Scholarship, she derived structure-activity relationships for a series of europium and terbium complexes with particular attention to their interactions with cells.

In 2010, Liz took up a fellowship from the Royal Commission for the Exhibition of 1851 to work at the University of California, Berkeley, with Associate Professor Chris Chang. Her project involved the design and synthesis of responsive sensors for studying copper ions in biological systems. In this work, she developed a ratiometric fluorescent sensor for Cu(I), and used it to discover new roles for copper in fat-storing cells. She also performed intracellular studies with an MRI sensor for Cu(I), measuring differences in copper accumulation in copper storage diseases.

Now with an ARC Discovery Early Career Researcher Award, Liz is establishing her own group. Her research interests lie in the area of chemical biology, which describes the application of chemical tools to study biology. This field has gained great momentum over the past decade, providing methods to study biological problems that could not otherwise be addressed. Innovations in this field include simple methods to fluorescently label proteins, small molecule fluorescent probes for biologically-interesting species, genetic incorporation of synthetic amino acids into proteins, and a range of bioorthogonal reactions that can occur in living systems that do not interfere with biochemical processes.

Liz’s particular interests lie at the development of small molecule responsive probes for various molecular imaging modalities including microscopy and MRI. Her aim is to design probes that respond selectively but reversibly, and report on the environment by some spectroscopic change.

The main research focus of the group will be the development of tools to study redox regulation in cells. Many diseases are associated with changes in redox state, so developing ways

to measure biological redox state will enable better understanding of these diseases and how they can be treated. By using flavins, which are used in nature in redox-sensing proteins, Liz’s group will prepare probes that can sense biologically-relevant changes in redox state.

Another interest of the group is the study of metal ions. Transition metals such as Zn, Cu, Ni, Fe and Mn play essential roles as cofactors in proteins, but there is also a less tightly-bound pool of metal ions that is now gaining interest. This metal pool is thought to play an important role in cellular signalling, but misregulation of levels can lead to diseases such as Alzheimer’s. The group will develop fluorescent probes for the study of this weakly-bound metal pool.

The work in Liz’s group will encompass synthesis of probes, photophysical characterisation, in vitro studies and preliminary biological investigation at the Australian Centre for Microscopy and Microanalysis. Through collaborations with medical researchers at Royal North Shore Hospital and cell biologists at Durham University, these tools will be applied to in vivo studies to gain important information about complex biological systems.

PRESTIGIOUS CLARENDON SCHOLARSHIP

PROFILE:DR ELIZABETH NEWThe main research focus of the New group will be the development of tools to study redox regulation in cells.

Last year Ms Anna Goldys (pictured left) won the internationally prestigious Clarendon Scholarship to undertake research towards a Doctor of Philosophy at the University of Oxford in the research group of Professor Darren Dixon. Anna was an outstanding Sydney graduate and University Medallist, who already had three publications from her time as a postgrad in the McErlean Research Group and has a further manuscript undergoing peer-review. We wish Anna all the best.

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Michela joined the School of Chemistry in December 2010. She received her BSc/Masters degree from the Victoria University of Manchester, UK in 2002. She went on to obtain her D.Phil. from the University of Oxford under the supervision of Professor George Fleet in 2006. Her project sponsored by the European Union, through an ERTN, focussed on the design and first systematic synthesis of branched carbohydrate lactones, which were then employed as versatile intermediates in the production of sugar amino acids, foldamers and iminosugars.

In 2007, Michela moved to University College London to work as a Postdoctoral Fellow in the Wolfson Institute for Biomedical Research under the guidance of Professor David Selwood. Her work covered several projects in the area of medicinal chemistry. In particular she contributed to the synthesis of a small molecular carrier (SMoC) class of biomolecule transporters, which were demonstrated to possess the ability to transfer functional siRNA into cells via supramolecular interactions.

In 2010, Michela went back to the University of Oxford where she held a short postdoctoral tenure (Feb.-Oct.) under the guidance of Professor Andrew Hamilton. During this time she worked in the area of molecular recognition targeted at the

disruption of particular protein-protein interactions. She then left the UK to join the School of Chemistry as Lecturer of Chemistry (Medicinal and Biological).

Michela is currently establishing her own group. Her research interests span from the synthesis and evaluation of novel classes of glycosidase inhibitors from carbohydrate starting materials to molecular recognition and supramolecular chemistry. Recently she has also moved into the area of bioinorganic chemistry primarily as relating to cancer research.

Carbohydrates are found ubiquitously in Nature where they represent a unique family of polyfunctional compounds which Nature extensively manipulates and finely tunes to serve a multitude of biological purposes. Carbohydrate building blocks provide a rich chiral pool of cheap, readily available and highly versatile starting materials for the enantiospecific synthesis of highly functionalised homochiral targets. They have recently been utilised in the synthesis of many classes of compounds, including iminosugars.

Iminosugars represent an important category of glycosidase inhibitors and proven to possess therapeutic potential in the management and treatment of many medical conditions, including diabetes, lysosomal storage diseases, viral infections and cancer. The amazing diversity of biological

roles found within this class of small molecules is evidence of a remarkable economy of structural information in nature, which in molecular weight terms completely surpasses anything achieved by the amino acids. The Simone group is

working in this burgeoning field of glycomimetics and undertaken the synthesis and evaluation of novel classes of iminosugars as anti-viral agents.

Another area of active research in the group is the fluorescent tagging of proteins. It is vital to biomedicine efforts to understand the spatial and temporal underpinnings of life inside cells in vivo versus in fixed cells. Current protein fluorescent tags are plagued by many draw-backs including excessive bulk, high toxicity, the need for extensive genetic engineering and the use of covalent bonds to link the sensor to the protein under investigation. These result in their limited use in vivo. We are undertaking the fluorescent tagging of proteins via innovative strategies, namely by the use of small fluorescent supramolecular entities which are engineered to transiently and selectively bind to the protein surfaces of interest.

After establishing of a number of collaborations with other scientists based at the University of Sydney, the Simone group has delved into the area of bioinorganic chemistry. The group is currently developing novel platinum- and cobalt-based compounds for evaluation as chemotherapeutics and novel 99mTc-based compounds which will be evaluated as cancer imaging agents.

After a rocky first year as an independent researcher, from now it’s onwards and upwards!

PROFILE:DR MICHELA SIMONEMichela’s research interests span from the synthesis and evaluation of novel classes of glycosidase inhibitors to molecular recognition and supramolecular chemistry. Recently she has also moved into the area of bioinorganic chemistry primarily as relating to cancer research.

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Congratulations to Dr Deanna D’Alessandro on winning a Young Tall Poppy Science Award from the Australian Institute of Policy and Science, announced at an awards ceremony on 3 November 2011. This prestigious annual science award recognises young scientists who are doing outstanding work in their field and are actively engaged in educating the community about their work. Dr D’Alessandro is developing ‘Metal-Organic Frameworks’ (or MOFs) to

capture and convert carbon dioxide emitted from power plants and natural gas wells. These materials have unique optical and electronic properties and can act as ‘molecular sponges’ to mop up greenhouse gases - one teaspoon full can have a surface area equivalent to an entire football field. They have the potential to significantly reduce the amount of carbon dioxide emitted by power plants and may help to reduce the penalty for capture using current technologies.

2011 END OF YEAR BASHThe School of Chemistry’s 2011 Christmas Party was enjoyed by all. It gave staff and students an opportunity to wind down after another busy year. The School would like to thank everyone who helped make this event such a success. More photos can be found on the Chemistry Facebook page.

YOUNG TALL POPPY AWARD

Dr Deanna D’Alessandro wins a Young Tall Poppy Science Award from the Australian Institute of Policy and Science.

100 YEARS OF ORGANIC CHEMISTRY FINAL REMINDER

A one-day reunion of the extended Organic Chemistry family is planned for Saturday, 3 November 2012. We hope that many former members and their families will be able to attend. Planned activities include a lunchtime barbecue, short talks from some former graduates of Organic Chemistry, a laboratory tour (which was your bench?), a display of posters of recent research and of historic memorabilia including the actual Nobel Prize diploma presented by King Gustav V of Sweden to Sir Robert Robinson in 1947.

Put the date in your diary now and watch out for further information. If you wish to receive regular updates regarding the reunion or have any further queries please email Dr Chris McErlean at christopher.mcerlean@sydney.edu.au or Professor Max Crossley at maxwell.crossley@sydney.edu.au

2 MINUTE CHEMISTRY ALUMNI

ONLINE SURVEY

The School of Chemistry is conducting an online survey to find out a bit more about you. We’d especially like to know if you would be interested in

attending chemistry events. This is also an opporunity to tell us what you think. This survey is design to take no more than

2 minutes to fill in and submit.

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http://bit.ly/A40934

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SCHOOL NEWS AND UPCOMING EVENTS

LEADING THE WAY IN SUSTAINABLE MANUFACTURINGBY MS KATHRYN KENNY, UNIVERSITY MEDIA OFFICE

Sustainable ways to produce plastics, foams, paints and other everyday materials could be the outcome of a $10 million, four-year project about to commence at the University of Sydney.

L-R: Professors Brian Haynes & Thomas Maschmeyer holding a bottle of biocrude oil.

Led by the University of Sydney’s Professor Thomas Maschmeyer, in a collaboration with the CSIRO, the project builds on his current research of deriving biocrude oil from sustainable fibrous (lignocellulosic) feedstocks, including forestry waste and seaweed, in a process that uses water at very high temperatures and high pressures. This new project will find ways to use the products that are created in addition to the biocrude oil.

“The process we use to make biocrude - called hydrothermal upgrading (HTU) - involves taking biomass and heating it in water to induce three things to occur: the generation of a spontaneously separating bio-oil, the production of gases and the synthesis of renewable chemicals dissolved in the aqueous phase,” explains Professor Maschmeyer.

Further, he states that these gases and chemicals could be put to a range of uses, including production of polyethylene and propylene that is commonly found in furniture and plastics, and material called aromatics that are used in resins, foams, rubbers, coatings, varnishes and solvents.

The project - Advanced Catalytic Processes for Renewable Chemicals Manufacture - is funded by a $5 million cash grant from the Science and Industry Endowment Fund (SIEF*), matched by $5 million in-kind funding from CSIRO and the University of Sydney.

At Sydney the research will be conducted together with Professor Brian Haynes, primarily at a purpose-built facility at the known as the NCRIS biomass reactor, using waste products already being generated by the timber industry as well as macro-algae (seaweed).

The second part of the project will be conducted by the CSIRO, focusing on enzymatic routes towards renewable chemicals as well as on the gaseous products of the HTU process.

Professor Maschmeyer predicts that in the future macro algae could provide the raw materials for this process in a

sustainable and renewable fashion. “Going offshore, into salt water, has the advantage of competing with neither current land, nor fresh water uses,” he says. In addition, it can help to bio-remediate large bodies of water like rivers, lakes and, especially pressing, the waters found between the Queensland coast and the Great Barrier Reef. Here, much run-off from the land is affecting the marine environment negatively. Native seagrasses could be used to reduce the nutrient levels in the water, while as a spin-off providing breeding habitat for various marine species and, of course, a sustainable source of renewable biomass. Combining these approaches also helps to improve the overall economics.

The project has the support of major industry players such as Lyondell-Basell, Dow Australia, Visy, Amcor, Ignite Energy

Resources and Licella, as well as the Department of Resources, Energy and Tourism and the Department of Innovation, Industry, Science and Research, with each of these entities having a seat on the project’s advisory board.

* www.sief.org.au

Please visit http://bit.ly/HP7m0z

FOR MORE INFORMATION CONTACT

Editor Professor Scott Kable

E scott.kable@sydney.edu.au

Enquires Ms Anne Woods

T +61 2 9351 2755

F +61 2 9351 3329

E anne.woods@sydney.edu.au

sydney.edu.au/science/chemistry

Printed on 100% recycled paper

SCHOOL OF CHEMISTRY

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Alpha Chemicals (Aust) P/L

Armstrong, A/Prof. Bob

Aroney, A/Prof. Manuel*

Atkins, Mrs Marie

Bacskay, Dr George

Bae, Ms Carol

Barlow, Dr Thomas

Beattie, A/Prof. James

Beck, Dr Walter H.

Bellas, Dr Thomas

Beratan, Prof David

Bishop, Dr Michael*

Boden, Mrs Elizabeth*

Broadhurst, A/Prof. Norm

Brown, Dr Roger F.C.

Buckingham, Prof. David

Chio, Mrs Hera LK

Collins, Dr David John

Collins, Dr Paul R

Cooper, Dr Merv

Coroneo, Andrew & Nicky

Corrie, Dr John

Coulson, Mrs Marion

Cowled, Mr Lance

Dawson, Dr Jeremy

Dimitriou, Mr Arthur

Docherty, Mr Reid William

Duckworth, Dr Paul

El Hassan, Mr Kaled

Felsobuki, Prof. Von Nagy

Fildes, Dr Joyce

Freeman family

Freisleben, Dr Seruni

Friend, Dr James

Gaspari, Mrs Sharyn

Geyer, Mr Robert

Goodrich, Dr Benjamin S.

Gready, Prof. Jill

Grieve, Dr Stuart M

Hacobian, Dr Steven

Hardy, Mr Andrew

Harle, Mr Alfred John

Heslop, Mrs Shirley

Hinde, Mr Ronald

Hukins, Dr Austin

Hunter, Dr Robert (Bob)

Huq, Dr Fazlul

Irvine, Mrs Sarah Jane

Judd, Dr Robert James

Jurox Pty Ltd

Kim, Mrs Eunho

King, Dr Phillip

Lambert-Smith, Dr John*

Larsson, Prof. Sven

Lastek Pty Ltd

Lay, Prof. Peter

Liedvogel, Mr Christian

Lim, A/Prof. Kieran

Lindoy, E/Prof. Len

Loch-Wilkinson, Dr Thorbjorn

Logan, Mr Colin

McInnes, Mr Rob

McLendon, Prof. George

Meyer, Thomas & Sandra

Napper, Prof. Don

Nell & Hermon Slade Trust

Newman, Dr Janet

O’Dwyer, Dr Michael F.

Pandelakis, Dr Spiros

Paton, Miss Nancy Hearne

Pavan, Mr Roberto

Peat, Dr Thomas

Petfield, Mr Gregory J W

Phillips, Dr Leo

Pidcock, Prof. Bettina

Pinhey, Prof. John T

Porter, Mrs M Jean

Ratner, Prof. Mark

Ridley, Dr Anne

Ryan, Mr W.P.

Savage, Mr Tom

Sheahan, Mr Thomas H.K.

Solomon, Dr Gemma

Sproule, Mrs Aileen

Stutchbury, Mr John

Suster, Mr John

Swanton, Dr David

Swe, Ms Thida

Temple, Dr Diana

Titapiwatanakun, Dr Umaporn

Vaughan, Dr Geoffrey

Wang, Mr Leo

Wang, Ms Lo-Chia

Ward, Mr Gregory

Warman, Dr C.H.

Whitelaw, Mr Ross

Willett, A/Prof. Gary

Williams, Dr Alan John

Woodhouse, Mr Ian

Woods, Ms Anne

Zdysiewicz, Dr JR

* Deceased

THANK YOU!The School would like to recognise the following Alumni and Friends for their generous support over the years and those who chose to remain anonymous.

Dr Jim Eckert returns with his fascinating articles on the history of the University, and in particular, the School of Chemistry. To read more please visit http://bit.ly/zy0kCN

THE CORNFORTH FUND

On the 10 August the Foundation held its 2011 Cornforth Lecture. Guest speaker was Professor Bert Meijer, Distinguished University Professor in Molecular Sciences and Professor of Organic Chemistry from the Eindhoven University of Technology, Eindhoven, The Netherlands. These lectures would not be possible without the generous donations of alumni and friends to which the Cornforth Foundation for Chemistry is very grateful.

Donations can be made to the Cornforth Fund by using the donation form provided or by using our online donation form at http://bit.ly/9hNHF3.

To read more about John Cornforth visit the Cornforth Foundation for Chemistry website at http://bit.ly/zvKpfp

Sir John Cornforth, Australian of the Year 1975

Sir John Warcup Cornforth, (1917 to present)

John Cornforth holds the prizes he has just received asdux of Sydney High in 1933

L-R: Professor Kate Jolliffe; Professor Bert Meijer and Dr Chris McErlean

Professor E.W. Meijer was born in Groningen, the Netherlands, in 1955. He studied at the University of Groningen, where he received his undergraduate degree in Chemistry in 1978. He obtained his PhD degree cum laude from the same university in 1982. Bert Meijer has performed his PhD research in the field of organic chemistry with a study on chemiluminescence of 1,2-dioxetanes under the supervision of Professor H. Wynberg. In the period 1982 - 1989 he was active as research chemist in the field of functional organic materials, including conducting polymers, at Philips Research Laboratories in Eindhoven. From 1989 till 1992 he was appointed as head of the department “New Materials” at DSM Research in Geleen, the Netherlands. From 1991 he is full professor in Organic Chemistry at the Eindhoven University of Technology and from 1995 he is also adjunct professor in Macromolecular Chemistry at the Nijmegen University. Bert Meijer was a visiting professor at the University of Leuven, Belgium (1995), the University of Illinois, Champaign-Urbana (1998) and the University of Florida, Gainesville, Florida (2003).

PROFESSOR E.W. “BERT” MEIJER

L-R: Professor Bert Meijer and Professor Thomas Maschmeyer

ABN 15 211 513 464 CRICOS 00026A

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