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Free Radical Reactions of Amino Acids, Peptides and Proteins
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Free radical reactions of amino acids, peptides and proteins are generally assumed to be omnipresent.
They are involved in many metabolic processes and associated with numerous physiological disorders,
such as Alzheimer's and heart disease. Consequently they have been studied extensively with
a view to their exploitation in understanding biochemical reactions and producing new drugs, as well as developing efficient synthetic methods.
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- Resistance of the α-amino acid and peptide structural motifs towards radical reactions
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We have used the chlorination of free and N-acetyl amino acids as models to quantify both the overall
reactivity of these molecules and the relative reactivity of each type of their hydrogens towards radical abstraction, which is one of the most common forms of their radical transformations.
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Investigating the reactivity of amino acids towards free radicals.
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The results show that the backbone and adjacent side chain positions of
amino acids derivatives are extensively deactivated towards reaction, as
a result of their location. This resistance to radical degradation may
have contributed to the evolution of peptides as the first biooligomers,
with the ability to persist under the harsh conditions of the prebiotic
atmosphere.
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Mr. Zhongqiang Wang
(PhD Student, November 2010-)
Research Interest: Investigations of unnatural amino acids in proteins.
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Mr. Mantas Liutkus
(PhD Student, February 2011-)
Research Interest: Investigations of unnatural amino acids in proteins.
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Mr. Sam Fraser
(PhD Student, March 2011-)
Research Topic: Incorporation of Unsaturated Isosteres of Aliphatic Amino Acids During Cell-Free Protein Synthesis
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Mr. Louis Moran
(PhD Student, February 2012-)
Research Topic: Inhibition studies on the BCAA biosynthesis pathway
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Beckwith memorial symposium on free radical chemistry.
Easton C.J., Aust. J. Chem ., 97 (2013), 66(3), 284-285.
DOI: 10.1071/CH13085
Reactivities of amino acid derivatives toward hydrogen abstraction by Cl• and OH•.
Chan B., O´Reilly R.J., Easton C.J., Radom L., J. Org. Chem.., (2012), 77(21), 9807-9812.
DOI: 10.1021/jo3021538
Incorporation of chlorinated analogues of aliphatic amino acids during cell-free protein synthesis.
Stigers, D. J., Watts, Z. I., Hennessy, J. E., Kim, H-K., Martini, R., Taylor, M. C., Ozawa, K., Keillor, J. W., Dixon, N. E. and Easton, C. J., Chem. Commun., (2011), 1839-1841.
DOI:10.1039/C0CC02879G
Peculiar Stability of Amino Acids and Peptides from a Radical Perspective.
Watts, Z. I. and Easton, C. J., J. Am. Chem. Soc., (2009), 131(32) 11323-11325.
DOI:10.1021/ja9027583
Design of Radical-Resistant Amino Acid Residues: A Combined Theoretical and Experimental Investigation.
Croft, A. K., Easton, C. J. and Radom, L., J. Am. Chem. Soc., (2003), 125, 4119-4124.
DOI:10.1021/ja029674v
Free Radical Reactions in the Synthesis of α-Amino Acids and Derivatives.
Easton, C. J., Chem. Rev., (1997), 97, 53-82.
DOI:10.1021/cr930048d
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Free radical chemistry and biotechnology
With C H Schiesser, J A Angus, R A J O'Hair, U Wille [U Melbourne],
L Radom, M J Davies [U Sydney], P J Scammels, W R Jackson [Monash U], S E Bottle [Queensland U Technology], P J Barker [BlueScope Steel], E Rizzardo [CSIRO Molecular
Health and Technologies, Melbourne], B Jarrott [Howard Florey Institute, Melbourne], C H Such [Orica Australia Pty Ltd], P Rogers [Carlton and United Breweries])
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