Dr Sandeep Handa

Dr Sandeep Handa

Associate Professor in Organic Chemistry
College Academic Director (Science & Engineering)
BA, PhD (Cambridge), FHEA
Tel : +44 (0)116 252 2128
Email : sh78@le.ac.uk
Research Group : Chemical Biology

Personal Details

  • BA, PhD (Cambridge)
  • Fellow of the Higher Education Academy

Current research projects are in the area of organic synthesis and its application to Chemical Biology and Green Chemistry. These projects cover many areas including the synthesis of biologically active molecules and the development of new synthetic methods.  Projects are multi-disciplinary involving contemporary organic synthetic and spectroscopic techniques as well as mechanistic chemistry.

Research Interests

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Novel CNS Agonists-Epibatidine Analogues

Novel CNS agonists are potential drugs for the relief of pain and the treatment of neurodegenerative disorders such as Alzheimer’s and Parkinson’s disease.  In this regard we are interested in the synthesis and biological activity of novel analogues of the natural product epibatidine that are potent and subtype selective N-acetylcholine receptor (nAChR) agonists.  We have reported our results with one such compound - isoepibatidine  and current studies are investigating the synthesis of fluorinated analogues.

SH 1

Publications

  1. ‘Approaches to syn-7-substituted 2-azanorbornanes as potential nicotinic agonists; Synthesis of syn- and ant-isoepibatidine’ Malpass, JR; Handa S; White R Org. Lett., 2005, 7, 2759-2762.
  2. ‘Epibatidine isomers and analogues: Structure-activity relationships’ White R; Malpass JR; Handa S; Baker, SR; Broad, LM; Folly, L; Mogg A Bioorg. & Med. Chem. Lett., 2006, 16, 5493-5497.

    Glycosidae Enzyme Inhibitors

    We are interested in the synthesis and biological activity of novel glycosidase inhibitors based on azasugars and have reported the asymmetric synthesis of a series of 3-aminopyrollidines.  We are also exploring the attachment of  a second aglycone-mimicking unit to generate aza-disaccharides. In related studies we have already synthesised a number of novel O - and N -linked aza-disaccharides employing complementary pinacol and ring closing metathesis (RCM) – dihydroxylation strategies. Our interest in glycosidase inhibitors also extends into the synthesis of novel calystegines.

    SH 2

    Publications

    1. Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl) pyrrolidines as potential glycosidase inhibitors’ Curtis KL;  Evinson EL; Handa S; Singh K Org. Biomol. Chem., 2007, 5, 3544 – 3553
    2. ‘The first syntheses of 6,7-dihydroxylated calystegines and homocalystegines' Groetzl, B; Handa, S; Malpass, JR Tetrahedron Lett. 2006, 47, 9147-9150.

      Enzyme Mechanisms of Tryptophan Oxidation

      We have been working with Professor Raven’s group to investigate the catalytic mechanism of heme peroxidase and dioxygenase enzymes.  Current focus is on the enzymes involved in the degradation of L-tryptophan to N-formylkynurenine, namely tryptophan 2,3-dioxygenase (TDO) and indoleamine 2,3-dioxygenase (IDO).  In this regard we have synthesised a number of potential intermediates on the degradation pathway for use in both turnover studies and as confirmation of their occurrence in the natural reaction.  The current focus is on application of our free-radical chemistry knowledge to design mechanism based inhibitors for both these enzymes.

      Publications

      1. ‘The Mechanism of Formation of N-Formylkynurenine by Heme Dioxygenases’ Basran J; Efimov, I; Chauhan, N; Thackray, SJ; Krupa, JL; Eaton, G; Griffith, GA; Mowat, CG; Handa, S; Raven EL J. Am. Chem. Soc., 2011, 133 (40), 16251–16257
      2. ‘Evidence for Heme Oxygenase Activity in a Heme Peroxidase’ Badyal, SK; Eaton, G; Mistry, S; Pipirou, Z; Basran J; Metcalfe, CL; Gumiero, A; Handa, S; Moody, PCE; Raven EL

      Mechanistic Free-radical Chemistry

      During the course of our synthetic projects we sometimes discover unusual or unexpected results that can lead to an intriguing insight into the mechanism of a particular reaction.  We are always keen to fully investigate these findings to shed some light on our observations.  Thus we have recently reported the use of cyclopropyl ketones to investigate the mechanism and rate of SmI2-mediated pinacol reactions.  We have also investigated novel free-radical mediated biomimetic 1,2-imino migrations.

      SH 3

      Publications

      1. ‘Samarium(II)iodide-mediated intramolecular pinacol coupling reactions with cyclopropyl ketones’ Foster SL.; Handa S; Krafft M; Rowling D Chem. Commun. 2007, 4791-4793.
      2. ‘Investigations into a free radical-mediated 1,2-imino migration’ Handa, S; Rose, CJ Tetrahedron Lett. 2004, 45, 8643-8645.

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      Contact Details

      Department of Chemistry
      University of Leicester
      Leicester, LE1 7RH, UK

      Email: chemistry@le.ac.uk

      Tel: [+44] (0)116 252 2100

      Fax: [+44] (0)116 252 3789

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