pphoto of dr alison edwards Dr Alison Edwards

BSc (Hons), DPhil, MRSC

Lecturer in Pharmaceutical Chemistry

Phone: +44 (0)1634 20 2947
Email: alison.edwards@gre.ac.uk

Alison obtained her BSc (Hons) in Chemistry from the University of Dundee in 1999 and received her DPhil from the University of Oxford in 2003. Prior to appointment at the Medway School of Pharmacy in November 2006, she held a postdoctoral researcher position at Imperial College London. Her research has focussed around the synthesis and study of sugar derived peptidomimetics (commonly known as sugar amino acids) and has published numerous papers in this area since 2003. Her research interests include the use of sugar amino acids to prepare analogues of biologically active small molecules and the study of conformational preference, with particular interest in chiroptical spectroscopy.

Specialist area: Organic chemistry

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Sugar amino acids (SAAs) are stereodiverse highly functionalised scaffolds which have been employed for a wide variety of uses including preparation of compound libraries, peptidomimetics and other novel analogues as potential drugs.  In addition to peptide mimicry, they have also been employed to mimic oligosaccharides, DNA and RNA.  Synthetically, the use of conventional carbohydrate building blocks can be problematic due to the issue of stereocontrol for formation of glycosidic linkages – an issue which can easily be circumvented for SAAs by use of an amide linkage.  The use of amide linkages has been exploited for peptide mimicry, where it has been observed that the conformational preference of the SAA unit can be key to the successful design of biologically active analogues. With this in mind, areas of interest are detailed below:

  • Utilisation of small molecular weight carbohydrates and SAAs for the preparation of novel drug candidates.
  • The development of new biomaterials such as hydrogels for pharmaceutical application.
  • The use of carbohydrates in multidisciplinary fields of chemistry and biology with emphasis on their exploitation as highly functionalised stereodiverse molecular scaffolds.
  • The study of peptidic and SAA systems, in particular to establish conformational preference and to investigate molecular interaction e.g. with probe molecules.
  • Developing new insight into the conformational understanding of biopolymer systems.
  • Utilisation of chiroptical spectroscopies, such as circular dichroism and Raman optical activity, for exploration of molecular interactions and the conformational study of biopolymer systems.
  • The interplay between molecular self-assembly, molecular structure and conformation.
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  • De Santis E, Hjelmgaard T, Caumes C, Faure S, Alexander BD, Holder SJ, Siligardi G, Taillefumier C, Edwards AA (2012). Effect of capping groups at the N- and C-termini on the conformational preference of α,β-peptoids. Org. Biomol. Chem.10(5): 1108 – 1122.
  • Hjelmgaard T, Faure S, De Santis E, Staerk D, Alexander BD, Edwards AA, Taillefumier C, Nielsen J (2012). Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains. Tetrahedron DOI: 10.1016/j.tet.2011.12.049.
  • De Santis E, Hjelmgaard T, Faure S, Roy O, Didierjean C, Alexander BD, Siligardi G, Hussain R, Jávorfi T, Edwards AA, Taillefumier C (2011). Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation. Amino Acids 41(3):663-672.
  • Simone MI, Edwards AA, Tranter GE, Fleet GWJF (2011) C-3 branched δ-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers. Amino Acids 41(3): 643-661.
  • Birchall LS, Roy S, Jayawarna V, Hughes M, Irvine E, Okorogheye GT, Saudi N, De Santis E, Tuttle T, Edwards AA, Ulijn RV (2011).  Exploiting CH-π interactions in supramolecular hydrogels of aromatic carbohydrate amphiphiles. Chemical Science 2(7): 1349-1355.  Selected to be on front cover of issue.
  • Al-Hamidi H, Edwards AA, Mohamman MA, Nokhodchi A (2010). To enhance dissolution rate of poorly water soluble drugs:  Glucosamine hydrochloride as a potential carrier in solid dispersion formulations. Colloids and Surfaces B: Biointerfaces 76(1): 170-178.
  • Al-Hamidi H, Edwards AA, Mohammad MA, Nokhodchi A (2010). Glucosamine HCl as a new carrier for improved dissolution behaviour: effect of grinding. Colloids and Surfaces B: Biointerfaces 81: 96-109.
  • Hjelmgaard T, Faure S, Caumes C, De Santis E, Edwards AA and Taillefumier C (2009). Convenient Solution-Phase Synthesis and Conformational Studies of Novel Linear and Cyclic α,β-Alternating Peptoids. Organic Letters 11(18): 4100-4103.
  • Simone MI, Edwards AA, Tranter GE, Fleet GWJ (2008). Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds. Tetrahedron: Asymmetry 19, 2887–2894.
  • Edwards AA, Alexander BD, Fleet GWJ, Tranter GE (2008). Spectroscopic studies of oligomers containing 2,5-trans furanoid sugar amino acids. Chirality 20: 969-972.
  • Edwards AA, Sanjayan GJ, Hachisu S, Tranter GE, Fleet GWJ (2006). A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry. Tetrahedron 62: 7718-7725.
  • Edwards AA, Sanjayan GJ, Hachisu S, Soengas R, Stewart A, Tranter GE, Fleet GWJ (2006). Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships. Tetrahedron 62: 4110-4119.
  • Bream R, Watkin DJ, Soengas R, Edwards AA, Hunter SJ, Tranter GE, Fleet GWJ (2006). Cyclo {[(6-amino-6-deoxy-2,3:4,5-di-o-isopropylidene-D-galactonic acid)-(D-Phe)]2}. Acta Crystallographica Section E E62: o1851-o1853.
  • Edwards AA, Fleet GWJ, Tranter GE (2006). Classification of conformation for sugar amino acid systems using chiroptical spectroscopy. Chirality 18: 265-272.
  • Claridge TDW, Long DD, Baker CM, Odell B, Grant GH, Edwards AA, Tranter GE, Fleet GWJ, Smith MD (2005). Helix-forming carbohydrate amino acids. Journal of Organic Chemistry 70: 2082-2090.
  • Johnson SW, Jenkinson (nee Barker) SF, Perez-Victoria I, Edwards A, Claridge TDW, Tranter G, Fleet GWJ, Jones JH (2005). Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. Journal of Peptide Science 11: 517-24.
  • Edwards AA, Fleet GWJ, Mayes BA, Hunter SJ, Tranter GE (2005). Circular dichroism studies of carbopeptoid-cyclodextrins. Chirality 17: S114-S119.
  • Mayes BA, Stetz RJE, Watterson MP, Edwards A, Ansell CWG, Tranter GE, Fleet GWJ (2004). Towards hydroxylated nylon 6: Linear and cyclic oligomers from a protected 6-amino-6-deoxy-D-galactonate - a novel class of carbopeptoid-cyclodextrin (CPCD). Tetrahedron: Asymmetry 15: 627-638.
  • Edwards AA, Ichihara O, Murfin S, Wilkes R, Whittaker M, Watkin DJ, Fleet GWJ (2004). Tetrahydrofuran-based amino acids as library scaffolds. Journal of Combinatorial Chemistry 6: 230-238.
  • Watterson MP, Edwards AA, Leach JA, Smith MD, Ichihara O, Fleet GWJ (2003). Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: C-glycosyl derivatives of 2-deoxy-ribose and precursors to tetrahydrofuran templated gamma-amino acids. Tetrahedron Letters 44: 5853-5857.

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