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Dr Luke Hunter

University of Sydney Postdoctoral Fellow

Contact Details

School of Chemistry, Building F11
University of Sydney, NSW, 2006, Australia
E-mail address: luke.hunter@sydney.edu.au
Telephone: +61-2-9114-1190
Fax: +61-2-9351-3329

Career Profile

  • BSc. (Adv.) (Hons.), University of Sydney, Australia (1997-2000)

  • PhD, University of Sydney, Australia (2001-2004)

  • Postdoctoral research associate, University of Melbourne, Australia (2005)

  • Postdoctoral research associate, University of St Andrews, UK (2005-2008)

  • Postdoctoral research associate, University of New South Wales, Australia (2008-2009)

  • University of Sydney Postdoctoral Fellow (2009-)

Areas of interest

  • Organofluorine chemistry and its application in shape-controlled peptides

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 (2008 - 2011)

  1. Hunter, L; Jolliffe, KA; Jordan, MJT; Jensen, P and Macquart, RB. Synthesis and conformational analysis of α,β-difluoro-γ-amino acid derivatives. Chemistry: A European Journal, 17 (8), 2340-2343, 2011. DOI: 10.1002/chem.201003320

  2. Hunter, L. The C–F bond as a conformational tool in organic and biological chemistry. Beilstein Journal of Organic Chemistry, 6 (38), 14 pp, 2010. DOI: 10.3762/bjoc.6.38

  3. Hunter, L; Kirsch, P; Slawin, AMZ and O'Hagan, D. Synthesis and structure of stereoisomeric multivicinal hexafluoroalkanes. Angew. Chem. Int. Ed., 48 (30), 5457-5460, 2009. DOI: 10.1002/anie.200901956

  4. Hunter, L and O'Hagan, D. Multi-vicinal fluoroalkanes: a new class of organofluorine compounds.  Org. Biomol. Chem., 6, 2843, 2008. DOI: 10.1002/chin.200847242

  5. Hunter, L; Kirsch, P; Hamilton, JTG and O'Hagan, D. The multi-vicinal fluoroalkane motif: an examination of 2,3,4,5-tetrafluorohexane stereoisomers. Org. Biomol. Chem., 6 (17), 3105-3108, 2008.