Andrew Clark Group

CITATIONS 2010 (98), CURRENT CITATIONS FOR 2011 to June 26th = 68,

CURRENT H-INDEX = 21

 

Our recent research covers these main areas of synthetic chemistry:

  • The development of new methodology and application to natural product synthesis using free radicals (including chemistry of enamides and ynamides).
  • The development of renewable resources as feedstocks for the chemical and polymer industries (including processing of waste products to valued added materials).
  • The application of chemical genetics tools to help in determining drug/receptor interactions

RENEWABLES and ELECTROSPINNING 2007-11:

Key Papers: 1) Macromol. Biosc. 2008, 8, 526, 2) Appl. Pol. Sci., 2010, 7, 116, 3) Resources, Conservation and Recycling 2011, doi.10.1016/j.resconrec

We were invited to give lecture tours of New Zealand and the US. We were invited by the Bioploymer Network of New Zealand to visit their Crop and Food Research establishment (contact. Dr. Nick Tucker) in 2007. Talks New Zealand 2007 (Radical), Talks New Zealand 2007 (Renewables). .

picture1.jpggb.jpgrapeseed.jpgpicture2.jpgF3 

Eco One Race Car World First Racing

 Eco-1 with me Eco-1 with G. Brown Rapeseed SEM of rape/hemp F3 FormulaFirst car

In collaboration with the Warwick Manufacturing Group and WarwickHRI we prepared materials from vegetable oils that were used in plastics found on the eco-car. The eco-car has appeared at the Eden Project, the Science Museum in Kensington, the Top Gear website and will soon be an exhibit at the Coventry Motor Museum. We will be building a fully racing Formula 3000 car in 2009. Recently, we prepared the fuel for the F3 WorldFirst Racing car. We recently were awarded two grants to continue work in the area of renewables. Adaptive Processing of Natural Feedtsocks: EPSRC EP/F015321/1 (£475,878). Wealth out of Waste: Warwick Innovative Manufacturing Research Centre (£324,000). We are working closely with Boots, Croda, Akzo Nobel and CI-KTN to exploit this research.

Recent published papers in this area 

  1. Extracting valuable compounds from straw degraded by pleurotus ostreatus, Res. Cons and Recy. 2011, in press
  2. A design of experiments (DoE) approach to material properties optimisation of electrospun nanofibres. S. R. Coles, D. K. Jacobs, G. Barker, A. J. Clark, K. Kirwan, J. App. Pol. Sci., 2010, 2251.
  3. Degradation studies of polyurethanes based on vegetable oils. Part 1.Photodegradation, A. Z. Mohd Rus, T. J. Kemp, A. J. Clark, Progress in Reaction Kinetics and Mechanism, 2008, 33, 363.
  4. Degradation studies of polyurethanes based on vegetable oils. Part 2. Thermal degradation and materials properties, A. Z. Mohd Rus, T. J. Kemp, A. J. Clark, Progress in Reaction Kinetics and Mechanism, 2009, 34, 1-41.
  5. Synthetic Mimicking of Plant Oils and Comparison with Naturally Grown Products in Polyurethane Synthesis, S. R. Coles, G. Barker, A. J. Clark, K. Kirwan, D. Jacobs, K. Makenji, D. Pink, Macromol. Biosci. 2008, 8, 526.
  6. Mechanical Properties of Hemp Fibre Reinforced Euphorbia Composites. A. J. Clark, N. J. Tucker, L. Mwaikambo. MacroMol. Mat. Engin. 2007, 292, 993-1000.

SYNTHETIC METHODOLOGY 2008-11: (Key Papers: 1) Journal of Organic Chemistry 2011, 2) Journal of Organic Chemistry 2009, 3) Journal of Organic Chemistry 2007 and 4) Tetrahedron Letters, 2008)

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We visited the labs of Prof. Dennis Curran at Pittsburg, Prof. Krzysztof Matyjaszewski of Carnegie Mellon and Prof. Ned Porter of Vanderbilt, (see talks usa).

Cyclisation (ATRC): Copper mediated atom transfer radical chemistry has recently been developed to overcome the problems associated with utilising toxic organotin hydrides in mediating radical cyclisation reactions. In this approach Cu(I) is used to abstract a halogen from a substrate (e.g. 6) to generate the radical 8. In this process the metal increases oxidation state, scheme 1. After cyclisation the metal then donates a halogen back to the cyclised radical 9 thus regenerating the active Cu(I) catalyst and retaining functionality in the product. In early studies this was low yielding, required high temperatures and only worked with activated precursors (e.g. trihalo derivatives such as 6). Better results were obtained when ligands for copper (e.g. ligands 1-5 above) were used in the reaction. We have applied this to the synthesis of beta and gamma lactams, Scheme 2 & 3. For more information on our copper based radical methodology click on this link.

 Recent published papers in this area

  1. Bond rotation dynamics of enamides: the effect of the acyl group and potential for chirality transfer during 5-endo radical cyclisations, A.J. Clark, D. P. Curran, J. V. Geden, N. James, P. Wilson, J. Org. Chem., 2011, in press doi 10.1021/jo200343z
  2. Copper(I) Halide Mediated Tandem 1,4-Aryl Migration / Oxidative 5-Exo Amidyl Radical Cyclisation of Bromosulfonamides. Andrew J Clark, David R. Fullaway, Nicholas P. Murphy, Hemal Parekh, Synlett, 2010, 610.
  3. Bond Rotation Dynamics of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives, D. B. Guthrie, K. Damodaran, D. P. Curran, P. Wilson, A. J. Clark, J. Org. Chem., 2009, 74, 4262.
  4. 1,4-Aryl migration under copper(I) atom transfer conditions. A. J. Clark, S. R. Coles, A. Collis, T. Debure, C. Guy, N.P Murphy, P. Wilson, Tetrahedron Letts., 2009, 50, 5609.
  5. Copper(I) bromide mediated 1,4-aryl migration of N-sulfonyl bromoacetamides, A. J. Clark, S. R. Coles, A. Collis, N.P Murphy, P. Wilson, Tetrahedron Letts., 2009, 50¸ 6311.
  6. Copper mediated atom transfer radical cyclisation with AIBN, Tetrahedron Letts., 2008, 49¸ 4848.
  7. Regiochemistry of Copper (I)-Mediated Cyclization of Dienamides. A. J. Clark, J. V. Geden, S. Thom, P. Wilson J. Org. Chem, 2007, 72, 5923-5926.
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CHEMICAL BIOLOGY AND Tangent Reprofiling.LTD 2008-11:

(Key Papers: 1) Mol. Biosyst. 2011, 7, 116. , 2) ChemMed, 2008, 3, 372

 Our Magic-Tag® technology (funded by BBSRC grant GR88/EGM17690) has recently been used to discover a putative interaction between β2-adrenoreceptor agonists and ATF4. A description of the technology can be found here (ChemCommun 2007, 2808).

 

 receptor magic tag kit 

 Recent published papers in this area

  1. Using the Man(9)(GlcNAc)-DC-SIGN pairing to probe specifity in photochemical immobilisaition. S. J. Dilly, A. J. Clark, D. A. Mitchell, A. Marhs, P. C. Taylor, Molecular Biosystem, 2011, 7, 116
  2. Rapid Identification of a Putative Interaction between b2-Adrenorecpetor Agonsits and ATF4 using a Chemical Genomics Approach, S. R. Ladwa, S. J. Dilly, A. J. Clark, A. Marsh, P. C. Taylor, ChemMedChem, 2008, 3, 372.
  3. Peptide / Protien identification using photoreactive carriers for immobilisation of the ligands. A. J. Clark, S. J. Dilly, A. Marsh, R. Napier, P. C. Taylor, Patent, 2007, WO/2007/020453, PCT/GB2006/003089
  4. Function and Stability of Abscisic Acid Acyl Hydrazone Conjugates by LC-MS2 of ex vivo Samples. T. Smith, A. J. Clark, R. Napier, P.C. Taylor, A. J. Thompson, A. Marsh, Bioconjugate Chemistry 2007, 18, 1355-1359.
  5. A Photoimobilisation Strategy that Maximises Exploration of Chemical Space in Small Molecule Affinity Selection and Target Discovery. S.J. Dilly, M. J. Bell, A. J. Clark, A. Marsh, R. Napier, M. J. Sergeant, A. J. Thompson, P.C. Taylor, Chem. Commun, 2007. 2808-2810.