Colin Raston

Last updated

Colin Llewellyn Raston

AO
Born1950 (age 72–73)
EducationBSc(Hons), PhD, DSc [1]
Alma mater University of Western Australia
Griffith University [1]
Occupation academic
Known for green, macrocyclic, and organometallic chemistry
TitleProfessor of Chemistry, Griffith University (1988–1994)
Professor of Chemistry, Monash University (1995–2000)
Professor of Chemistry, The University of Leeds (2001–2002)
Professor of Chemistry, The University of Western Australia (2003–2012)
Professor of Clean Technology, Flinders University (2013– ) [1]
AwardsBurrows Award, 1994 [2]
H G Smith Memorial Medal, 1996 [1]
Green Chemistry Challenge Award, 2002 [2]
Leighton Memorial Medal, 2006 [2]
RACI Living Luminary, 2011 [2]
South Australia Premier's Professorial Research Fellow in Clean Technology, 2013 [1]
Ig Nobel Prize in Chemistry, 2015 [3]
Officer of the Order of Australia, 2016 [4]

Colin Llewellyn Raston AO FAA (born 1950) is a Professor of Chemistry of Flinders University in Adelaide, South Australia and the Premier's Professorial Fellow in Clean Technology. [1] In 2015, he was awarded an Ig Nobel Prize in "for inventing a chemical recipe to partially un-boil an egg". [3] In 2016, Raston was made an Officer of the Order of Australia for his services to science. [4]

Contents

Research work

Early career

Chemical structure of arsenobetaine ArsenobetainePIC.svg
Chemical structure of arsenobetaine

Raston undertook his early tertiary studies at the University of Western Australia, taking a bachelor degree in science with honours and a doctor of philosophy under Professor Allan White. [1] Raston's work included looking at marine organoarsenic compounds, isolating arsenobetaine from the Western Rock Lobster and determining its structure and synthesis. [5] This zwitterionic substance turns out to be the main source of arsenic in fish [6] and unlike other arsenic compounds (like dimethylarsine and trimethylarsine) it has comparatively low toxicity. [7] Arsenobetaine is an analog of betaine (trimethylglycine) and with similar biosynthesis to choline and betaines. [8]

He later received a higher doctorate (Doctor of Science) from Griffith University. [1]

Calixarenes

Calix[4]arene with para-tert-butyl substituents and a hydrophobic cavity formed by the phenyl groups. Hydrogen bonding between the hydroxyl groups stabilises the 'base' of the chalice. Calixarene.png
Calix[4]arene with para-tert-butyl substituents and a hydrophobic cavity formed by the phenyl groups. Hydrogen bonding between the hydroxyl groups stabilises the 'base' of the chalice.

Resorcinarene is a macrocycle typically prepared by the condensation of resorcinol and formaldehyde in an acidic environment. Multiple isomers are possible when any other aldehyde is used and different conditions, including Lewis acid catalysis have been employed to minimise by-products. [9] [10] Raston and co-workers have developed an alternative green chemistry solvent-free approach whereby resorcinol and the aldehyde are ground together with p-toluenesulfonic acid in a mortar and pestle and the product recrystallised from the resulting paste. [11]

Resorcinarene synth.svg

Calixarenes are the general category of macrocycle oligomers formed by hydroxyalkylation of a phenol and an aldehyde; [12] Resorcinarenes are one example. Calixarenes resemble chalices (calix in Latin) with hydrophobic cavities that can hold smaller molecules or ions, an example of host–guest chemistry. Raston has demonstrated a green chemistry approach to pyrogallol[4]arene from isovaleraldehyde (3-methylbutanal) and pyrogallol (1,2,3-benzenetriol) with a catalytic amount of p-toluenesulfonic acid. [11] He also produced a ball-and-socket supramolecular complex where calix[5]arene hosts the C70 fullerene. [13] The five phenyl groups forming the walls of the cavity interact with the aromatic fullerene through π stacking.

Unboiling an egg

Ovalbumin is the protein which makes up around two-thirds of the white of an egg. [14] When an egg is cooked, the ovalbumin changes conformation from its folded and soluble form to an insoluble all-β-sheet structure with exposed hydrophobic regions, leading to aggregation. [15] This is a classic example of protein denaturation, defined as the loss of the quaternary, tertiary and secondary structures that are present in the protein's native state, by application of some external chemical or radiative stress (including heat). [16] In order to "unboil" the egg, the individual protein strands must be separated from the aggregate and then re-folded back to their native form. [17] Raston had the idea of using mechanical energy from spinning the aggregate to achieve this and developed vortex fluidic technology to implement his idea. [18] Using it to unboil an egg (at least in part) was meant as a demonstration of the technology and won Raston and colleagues the 2015 Ig Nobel Prize in chemistry. [3] Applications of the technology include boosting the potency of anti-cancer drugs like carboplatin [19] and improving the production of biodiesel. [20]

Honours and awards

Raston was recognised for his professional achievements with Fellowships in the Royal Australian Chemical Institute (RACI) and the Royal Society of Chemistry. [1] On 13 June 2016, Governor-General, Sir Peter Cosgrove announced that Raston had been made an Officer of the Order of Australia in the Queen's Birthday Honours List, for "distinguished service to science through seminal contributions to the field of chemistry as a researcher and academic, and to professional associations". [4]

Raston served as the Vice President of the RACI in 1995–96, winning the H. G. Smith Memorial Medal that year, [1] and went on to serve as President the following year. [2] He has received several RACI awards, including the Burrows Award in 1994, which is the premier award of the Inorganic Chemistry Division of the RACI. In 2002, he was recognised with the Green Chemistry Challenge Award and went on to take the Leighton Memorial Medal, [2] the institute's most prestigious medal given in recognition of eminent services to chemistry in Australia, in 2006. He was named an RACI Living Luminary and in 2013 was appointed as the South Australia Premier's Professorial Research Fellow in Clean Technology. [1] Raston is also the founding co-chair of the RACI Green and Sustainable Chemistry (GASC) National Group. [21]

In 2018, Raston was elected Fellow of the Australian Academy of Science (FAA). [22]

Related Research Articles

<span class="mw-page-title-main">Organometallic chemistry</span> Study of organic compounds containing metal(s)

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.

The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.

The aldol reaction is a reaction that combines two carbonyl compounds to form a new β-hydroxy carbonyl compound.

<span class="mw-page-title-main">Aldol condensation</span> Type of chemical reaction

An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties react to form a β-hydroxyaldehyde or β-hydroxyketone, and this is then followed by dehydration to give a conjugated enone.

Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component. While traditional chemistry concentrates on the covalent bond, supramolecular chemistry examines the weaker and reversible non-covalent interactions between molecules. These forces include hydrogen bonding, metal coordination, hydrophobic forces, van der Waals forces, pi–pi interactions and electrostatic effects.

<span class="mw-page-title-main">Resorcinol</span> Chemical compound

Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.

<span class="mw-page-title-main">Ovalbumin</span> Main protein found in egg white

Ovalbumin is the main protein found in egg white, making up approximately 55% of the total protein. Ovalbumin displays sequence and three-dimensional homology to the serpin superfamily, but unlike most serpins it is not a serine protease inhibitor. The function of ovalbumin is unknown, although it is presumed to be a storage protein.

A calixarene is a macrocycle or cyclic oligomer based on a methylene-linked phenols. With hydrophobic cavities that can hold smaller molecules or ions, calixarenes belong to the class of cavitands known in host–guest chemistry.

<span class="mw-page-title-main">Cavitand</span> Molecule able to contain another molecule within itself

In chemistry, a cavitand is a container-shaped molecule. The cavity of the cavitand allows it to engage in host–guest chemistry with guest molecules of a complementary shape and size. The original definition proposed by Cram includes many classes of molecules: cyclodextrins, calixarenes, pillararenes and cucurbiturils. However, modern usage in the field of supramolecular chemistry specifically refers to cavitands formed on a resorcinarene scaffold by bridging adjacent phenolic units. The simplest bridging unit is methylene, although dimethylene, trimethylene, benzal, xylyl, pyridyl, 2,3-disubstituted-quinoxaline, o-dinitrobenzyl, dialkylsilylene, and phosphonates are known. Cavitands that have an extended aromatic bridging unit, or an extended cavity containing 3 rows of aromatic rings are referred to as deep-cavity cavitands and have broad applications in host-guest chemistry. These types of cavitands were extensively investigated by Rebek, and Gibb, among others.

In chemistry, a resorcinarene is a macrocycle, or a cyclic oligomer, based on the condensation of resorcinol (1,3-dihydroxybenzene) and an aldehyde. Resorcinarenes are a type of calixarene. Other types of resorcinarenes include the related pyrogallolarenes and octahydroxypyridines, derived from pyrogallol and 2,6-dihydroxypyridine, respectively.

Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungicides. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are arsane and arsenic acid. Despite their toxicity, organoarsenic biomolecules are well known.

<span class="mw-page-title-main">Arsenobetaine</span> Chemical compound

Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish. It is the arsenic analog of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are similar to those of choline and betaine.

<span class="mw-page-title-main">Rothemund reaction</span>

The Rothemund reaction is a condensation/oxidation process that converts four pyrroles and four aldehydes into a porphyrin. It is based on work by Paul Rothemund, who first reported it in 1936. The method underpin more modern synthesis such as those described by Adler and Longo and by Lindsey. The Rothemund reactions is common in university teaching labs.

<span class="mw-page-title-main">Propionaldehyde</span> Chemical compound

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially.

Metal-catalyzed C–H borylation reactions are transition metal catalyzed organic reactions that produce an organoboron compound through functionalization of aliphatic and aromatic C–H bonds and are therefore useful reactions for carbon–hydrogen bond activation. Metal-catalyzed C–H borylation reactions utilize transition metals to directly convert a C–H bond into a C–B bond. This route can be advantageous compared to traditional borylation reactions by making use of cheap and abundant hydrocarbon starting material, limiting prefunctionalized organic compounds, reducing toxic byproducts, and streamlining the synthesis of biologically important molecules. Boronic acids, and boronic esters are common boryl groups incorporated into organic molecules through borylation reactions. Boronic acids are trivalent boron-containing organic compounds that possess one alkyl substituent and two hydroxyl groups. Similarly, boronic esters possess one alkyl substituent and two ester groups. Boronic acids and esters are classified depending on the type of carbon group (R) directly bonded to boron, for example alkyl-, alkenyl-, alkynyl-, and aryl-boronic esters. The most common type of starting materials that incorporate boronic esters into organic compounds for transition metal catalyzed borylation reactions have the general formula (RO)2B-B(OR)2. For example, bis(pinacolato)diboron (B2Pin2), and bis(catecholato)diborane (B2Cat2) are common boron sources of this general formula.

The aldehyde tag is a short peptide tag that can be further modified to add fluorophores, glycans, PEG chains, or reactive groups for further synthesis. A short, genetically-encoded peptide with a consensus sequence LCxPxR is introduced into fusion proteins, and by subsequent treatment with the formylglycine-generating enzyme (FGE), the cysteine of the tag is converted to a reactive aldehyde group. This electrophilic group can be targeted by an array of aldehyde-specific reagents, such as aminooxy- or hydrazide-functionalized compounds.

Clark Landis is an American chemist, whose research focuses on organic and inorganic chemistry. He is currently a Professor of Chemistry at the University of Wisconsin–Madison. He was awarded the ACS Award in Organometallic Chemistry in 2010, and is a fellow of the American Chemical Society and the American Association for the Advancement of Science.

A pyrogallolarene is a macrocycle, or a cyclic oligomer, based on the condensation of pyrogallol (1,2,3-trihydroxybenzene) and an aldehyde. Pyrogallolarenes are a type of calixarene, and a subset of resorcinarenes that are substituted with a hydroxyl at the 2-position.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 "Professor Colin Raston". Flinders University . Retrieved 16 June 2016.
  2. 1 2 3 4 5 6 "Royal Australian Chemical Institute Awards and Office Bearers". Royal Australian Chemical Institute. Archived from the original on 7 March 2016. Retrieved 15 June 2016.
  3. 1 2 3 "Improbable Research – The 2015 Ig Nobel Prize Winners". www.improbable.com. 17 September 2015. Retrieved 15 June 2016.
  4. 1 2 3 "The Queen's Birthday 2016 Honours List: Officer (AO) in the General Division of the Order of Australia" (PDF). Governor-General of the Commonwealth of Australia. p. 41. Archived from the original (PDF) on 15 June 2016. Retrieved 14 June 2016.
  5. ↑ Edmonds, J. S.; Francesconi, K. A.; Cannon, J. R.; Raston, C. L.; Skelton, B. W.; White, A. H. (1977). "Isolation, crystal structure and Synthesis of arsenobetaine, the arsenical constituent of the Western Rock Lobster Panulirus longipes cygnus George". Tetrahedron Letters . 18 (18): 1543–1546. doi:10.1016/S0040-4039(01)93098-9.
  6. ↑ Francesconi, K. A. (2005). "Current perspectives in arsenic environmental and biological research". Environmental Chemistry . 2 (3): 141–145. doi:10.1071/EN05042.
  7. ↑ Bhattacharya, P.; Welch, A. H.; Stollenwerk, K. G.; McLaughlin, M. J.; Bundschuh, J.; Panaullah, G. (2007). "Arsenic in the environment: Biology and chemistry". Science of the Total Environment . 379 (2–3): 109–120. Bibcode:2007ScTEn.379..109B. doi:10.1016/j.scitotenv.2007.02.037. PMID   17434206.
  8. ↑ Adair, B. M.; Waters, S. B.; Devesa, V.; Drobna, Z.; Styblo, M.; Thomas, D. J. (2005). "Commonalities in metabolism of arsenicals". Environmental Chemistry . 2 (3): 161–166. doi:10.1071/EN05054.
  9. ↑ Högberg, A. G. S. (1980). "Two stereoisomeric macrocyclic resorcinol-acetaldehyde condensation products". Journal of Organic Chemistry . 45 (22): 4498–4500. doi:10.1021/jo01310a046.
  10. ↑ Högberg, A. G. S. (1980). "Cyclooligomeric phenol-aldehyde condensation products. 2. Stereoselective synthesis and DNMR study of two 1,8,15,22-tetraphenyl[14]metacyclophan-3,5,10,12,17,19,24,26-octols". Journal of the American Chemical Society . 102 (19): 6046–6050. doi:10.1021/ja00539a012.
  11. 1 2 Antesberger, J; Cave, G. W.; Ferrarelli, M. C.; Heaven, M. W.; Raston, C. L.; Atwood, J. L. (2005). "Solvent-free, direct synthesis of supramolecular nano-capsules". Chemical Communications . 2005 (7): 892–894. doi:10.1039/b412251h. PMID   15700072.
  12. ↑ Gutsche, C. D. (1989). Calixarenes. Cambridge: Royal Society of Chemistry. ISBN   085186385X.
  13. ↑ Atwood, J. L.; Barbour, L. J.; Heaven, M. W.; Raston, C. L. (2003). "Association and orientation of C70 on complexation with calix[5]arene". Chemical Communications . 2003 (18): 2270–2271. doi:10.1039/B306411P. PMID   14518869.
  14. ↑ Huntington, J. A.; Stein, P. E. (2001). "Structure and properties of ovalbumin". Journal of Chromatography B . 756 (1–2): 189–198. doi:10.1016/S0378-4347(01)00108-6. PMID   11419711.
  15. ↑ Hu, H. Y.; Du, H. N. (2000). "α-to-β Structural transformation of ovalbumin: Heat and pH effects". Journal of Protein Chemistry . 19 (3): 177–183. doi:10.1023/A:1007099502179. PMID   10981809. S2CID   82745511.
  16. ↑ Mosby's Medical Dictionary (9th ed.). Elsevier. 2009. Retrieved 14 June 2016.
  17. ↑ Yuan, T. Z.; Ormonde, C. F. G.; Kudlacek, S. T.; Kunche, S.; Smith, J. N.; Brown, W. A.; Pugliese, K. M.; Olsen, T. J.; Iftikhar, M.; Raston, C. L.; Weiss, G. A. (2015). "Shear-stress-mediated refolding of proteins from aggregates and inclusion Bodies". ChemBioChem . 16 (3): 393–396. doi:10.1002/cbic.201402427. PMC   4388321 . PMID   25620679.
  18. ↑ Seidel, J. (23 September 2015). "Over-cooked? Flinders University professor Colin Raston gets Ig Nobel Prize for 'unboiling an egg'". news.com.au. News Corporation . Retrieved 14 June 2016.
  19. ↑ Strom, M. (22 May 2015). "Machine that 'uncooks eggs' used to improve cancer treatment". Sydney Morning Herald . Retrieved 14 June 2016.
  20. ↑ Eacott, A. (22 May 2015). "Cancer drug more effective after use of vortex fluidic device invented by Australian researcher". abc.net.au. ABC (Australia) . Retrieved 14 June 2016.
  21. ↑ "Green and Sustainable Group". raci.org.au. Retrieved 27 February 2023.
  22. ↑ "Professor Colin Raston". www.science.org.au. Retrieved 16 June 2018.
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