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Academic Research Staff: Luke Hunter
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University of Sydney Postdoctoral Fellow
Address:
School of Chemistry, Building F11
University of Sydney, NSW, 2006, Australia
E-mail address: l.hunter@chem.usyd.edu.au
Telephone: +61-2-9114-1190
Fax: +61-2-9351-3329
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Career Profile:
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BSc. (Adv.) (Hons.), University of Sydney, Australia (1997-2000)
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PhD, University of Sydney, Australia (2001-2004)
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Postdoctoral research associate, University of Melbourne, Australia (2005)
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Postdoctoral research associate, University of St Andrews, UK (2005-2008)
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Postdoctoral research associate, University of New South Wales, Australia (2008-2009)
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University of Sydney Postdoctoral Fellow (2009-)
Areas of interest:
Research:
Fluorine is the most electronegative element in the periodic table, and it has a dramatic impact when incorporated into organic molecules. The highly polarised C-F bond participates in a variety of stereoelectronic interactions with neighbouring functional groups, and these interactions can be exploited to control molecules’ 3D conformations.
My current research focuses on the synthesis of unnatural amino acids containing two or more vicinal (adjacent) fluorine atoms. Such molecules adopt unique well-defined conformations, dictated by the fluorine stereochemistry. These fluorinated amino acids will be valuable building blocks for incorporation into shape-controlled peptides. As an illustration of this concept, I am investigating the synthesis of bent peptides designed to undergo head-to-tail cyclisation in high yield. Another avenue of research is the preparation of fluorinated RGD peptides which are conformationally “fine-tuned” for selective biological activity.
Publications:
Synthesis and structure of stereoisomeric multi-vicinal hexafluoroalkanes. Hunter L., Kirsch P., Slawin A.M.Z., O’Hagan D., Angew. Chem. Int. Ed. 2009, in press.
Multi-vicinal fluoroalkanes: a new class of organofluorine compounds. Hunter L., O’Hagan D., Org. Biomol. Chem. 2008, 6, 2843.
The multi-vicinal fluoroalkane motif: an examination of 2,3,4,5-tetrafluorohexane stereoisomers. Hunter L., Kirsch P., Hamilton J.T.G., O'Hagan D., Org. Biomol. Chem. 2008, 6, 3105.
Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers. Hunter L., Kirsch P., Slawin A.M.Z., O’Hagan D., Angew. Chem. Int. Ed. 2007, 46, 7887.
Enantioselective synthesis of an all-syn four vicinal fluorine motif. Hunter L., Slawin A.M.Z., O’Hagan D., J. Am. Chem. Soc. 2006, 128, 16422.
Synthesis of the β-hydroxydopa-γ-hydroxy-δ-sulfinylnorvaline component of ustiloxins A and B. Hunter L., McLeod M.D., Hutton C.A., Org. Biomol. Chem. 2005, 3, 732.
Highly enantioselective recombinant thermoalkalophilic lipases from Geobacillus and Bacillus sp. Hutchins L., Hunter L., Ehya N., Gibbs M.D., Bergquist P.L., Hutton C.A., Tetrahedron: Asymmetry 2004, 15, 2975.
Preparation of selectively protected L-DOPA derivatives: oxidation of tyrosine-3-boronates. Hunter L., Hutton C.A., Aust. J. Chem. 2003, 56, 1095.
Biochemical characterization of a recombinant thermoalkalophilic lipase and assessment of its substrate enantioselectivity. Sunna A., Hunter L., Hutton C.A., Bergquist P.L., Enzyme Microb. Technol. 2002, 31, 472. |
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