Teachers Notes - Professor John Swan

Organic chemist

Contents

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Introduction

Professor John Swan was interviewed in 2008 for the Interviews with Australian scientists series. By viewing the interviews in this series, or reading the transcripts and extracts, your students can begin to appreciate Australia's contribution to the growth of scientific knowledge.

The following summary of Swan's career sets the context for the extract chosen for these teachers notes. The extract presents a sample of chemical investigations from Swan’s career that he found particularly satisfying. Use the focus questions that accompany the extract to promote discussion among your students.

Summary of career

John Swan was born in Melbourne, in 1924. He left school in 1940 and worked as a junior laboratory assistant at ICIANZ in an explosives factory, analysing chemicals used in war munitions. He took night classes at the Royal Melbourne Technical College (now RMIT University) and completed a diploma in applied chemistry in 1944. He continued his studies at the University of Melbourne and received a BSc in 1947. Awarded a CSIR (now the CSIRO) scholarship, he studied at the University of London and was awarded a PhD in 1949.

On his return to Australia, Swan worked as a chemist at the CSIR from 1949 to 1965. He researched a number of interesting projects during these years including understanding the chemical and physical properties of the wool protein, breaking disulphide bonds between amino acids and producing ethylene for use as a ripening agent. During 1953 he was a Fulbright scholar at the Cornell University Medical College, New York, where he was involved in the synthesis of the peptide hormone oxytocin, the structure of which had just recently been discovered.

In 1966 Swan moved to Monash University as professor of organic chemistry. From 1971 to 1975 he served as pro vice-chancellor at the university. He became dean of the Faculty of Science in 1976 and remained in this position until 1984. After his retirement, he was appointed as an emeritus professor at the university. Swan was awarded a DSc from Monash University in 1994.

During his Monash years, Swan became involved in marine and environmental issues. This interest continued after his retirement. He has had appointments to the CRC for Southern Hemisphere Meteorology, the Westernport Region Water Authority and the Victorian Coastal Council. He has also served on the scientific advisory committee of the Port Phillip Bay Environmental Study and as a director of the Western Port Seagrass Partnership.

Swan has received numerous honours over his career including the ANZAAS Medal (1994), the HG Smith Medal (1965) of the Royal Australian Chemical Institute and the David Syme Research Prize from the University of Melbourne (shared in 1965). He is a Fellow of the Royal Australian Chemical Institute (1955) and a Fellow of the Australian Academy of Technological Sciences and Engineering (1994). He was made an Officer of the Order of Australia in 2002 and received the Australia Centenary Medal in 2001.

Swan was elected a Fellow of the Australian Academy of Science in 1968.

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Extract from interview

Looking back over your very long and distinguished career, John, which particular things in chemistry would you say gave you the greatest satisfaction?

Oh, gosh. I hope you won't find this too long a list! First I'd have to go back to the war time, when in that fourth year of my employment I worked on the sulfamerazine project. That was interesting.

In the end of that year, I can well remember, Dr Finn came into my laboratory one morning and said, 'We've just been sent this very interesting patent from Switzerland, of an amazing new insecticide called DDT. Here's a description of how to make it.' So by lunchtime I had made 50 grams of DDT. By the end of that year, ICI was making a tonne a week down at Yarraville. It really was a remarkably successful insecticide and it still is, despite all the negative publicity about it – I won't go into all the details, but it still has a role to play, particularly on indoor surfaces of houses in Africa. You don't spray it all over the countryside, but you can make the inside of your house virtually lethal to mosquitoes with an extremely cheap and easily manufactured chemical, which isn't quite as bad as it has been painted. To be involved in that was another interesting experience.

One of the things I did when I was with CSIRO in the early days was to find a new method for breaking the disulphide bond, which is such an important feature of all proteins, by a method which we called 'oxidative sulphitolysis'. You could simply cleave the sulphur-sulphur linkage with a mixture of sodium sulphite and an oxidising agent. That was quite an important breakthrough in the way to unravel the proteins before doing other chemistry to them.

I have spoken briefly about synthesising oxytocin. When we were doing that work, oxytocin was used only – but widely – for initiating childbirth. The only supply of this chemical that was available for the purpose was human oxytocin, obtained from pituitary glands of deceased people, and was always contaminated with a very closely related peptide called vasopressin. Unfortunately, vasopressin, in addition to being an important hormone to let down the milk for a lactating mother, causes the blood pressure to rise, and the last thing the obstetrician wants when he gives oxytocin is contamination with another hormone that will cause blood pressure to rise. The synthesis of oxytocin made it possible for the chemical industry to make pure oxytocin without contamination, and that work was interesting.I have been amused to see in recent years that oxytocin has now got a far wider coverage of public awareness. If you'll allow me, I'll read you something about oxytocin from a recent scientific article:

It has been called the love hormone, the cuddle chemical and liquid trust. It peaks with orgasm, makes a loving touch magically melt away stress and increases generosity when given as a drug. Oxytocin is the essence of affection itself, the brain chemical that warmly bonds parent to child, lover to lover, friend to friend, and it could soon be unleashing its loved-up powers far and wide.

Would you believe this?

Oxytocin, they go on to say, has long been used in labour and so on, but it's now become a very interesting chemical in the functioning of the brain and the whole gamut of human emotions to do with friendship, which I find intriguing. [laugh]

It sounds as if we should be spraying people with oxytocin!

Well, yes. Among other interesting and satisfying things, while I was with CSIRO I found a new method for making alkenes by rapidly breaking down, very easily and at very high yield, chemicals called 2-chloro-alkyl phosphonic acids. This was even employed by one food company in America, because ethylene is a gas which promotes the ripening of fruit, and all fruits when they ripen naturally give off ethylene. If you've got a cool store with 10,000 bananas or whatever in it and you want them to ripen more quickly, you can release ethylene into it. Because not everybody can handle gaseous ethylene or if they don't like doing it that way, you could use my chemical 2-chloro-alkyl phosphonic acid, drop it into sodium bicarbonate and generate ethylene in a chemical way. That was actually used in some places in America for food ripening.

Focus questions

  • Swan's work has often been with the synthesis or construction of organic chemicals. Can you list two compounds which he has helped to synthesise?
  • Why is oxytocin sometimes referred to as the 'love hormone'?
  • What are peptides?

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Activities

Select activities that are most appropriate for your lesson plan or add your own. You can also encourage students to identify key issues in the preceding extract and devise their own questions or topics for discussion.

  • Oxytocin and vasopressin are both peptide hormones. Have students use library and internet resources to find out more about different peptide hormones. They should learn about the peptide hormone's chemical structure, its effect in the body, medical conditions that are caused by a lack of it and any interesting information about the history of its discovery. They present their findings as a short written or oral report.

  • Swan is an organic chemist but there are many different special areas of chemistry. Have students investigate different types of chemistry and present their findings as a short written report.

  • Organic compounds (Access Excellence, USA)
    Laboratory activity for students to identify different biological molecules in a variety of foods.

  • Chemical changes (The Educator's Reference Desk, USA)
    Students explore how chemical reactions produce new substances.

  • Yes, we have ripe bananas (Education World, USA)
    Students investigate factors that help bananas ripen or not. Discussion leads to the role of ethylene as a ripening hormone.

  • Chemical reactions and how you know when you've made something new (Chemical Heritage Foundation, USA)
    In this lab activity, students will learn not only how to synthesise a compound but will also learn some basic tests to determine that the product is different from the starting chemicals (reactants). Synthetic vs. Natural: What's the Difference? is a reading to accompany this activity. This activity is part of a project called Science Alive! which connects history and the nature of science with chemical concepts taught in schools.

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Keywords

amino acid
chemical synthesis
ethylene
organic chemistry
oxytocin
peptide hormone
protein

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