Medway school of pharmacy

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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• Thomas Hjelmgaard, Sophie Faure, Ce´cile Caumes, Emiliana De Santis,
  Alison A. Edwards and Claude Taillefumier. Convenient Solution-Phase Synthesis and Conformational Studies of Novel Linear and Cyclic a,b Alternating Peptoids. Organi c Letters 2009, 11 (18), 4100-4103.
• Simone MI, Edwards AA, Tranter GE and Fleet GWJ (2008). Carbon-branched d-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 Crystallogr Sect E-Struct Rep Online 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. J Org Chem 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. J Pept Sci 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. J Comb Chem 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 Lett 44: 5853-5857.

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