Biography

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Dr Bew graduated with a BSc in Chemistry from the University of Leicester. He subsequently moved to the School of Chemistry at the University of Bristol where he undertook his PhD under the supervision of Professor J. B. Sweeney. His PhD was concerned with the synthesis of organotin derived 3-sulpholenes, their cheletropic properties and cycloaddition chemistry. Upon completing his studies he undertook postdoctoral research at the University of Bath, working on the development of novel 2-nitroimidazole containing Boron Neutron Capture Agents (BNCT) for anticancer applications. Completing his studies at Bath he moved to the Schools of Chemistry at The University of Nottingham and subsequently to the University of Wales (Cardiff, both with professor D. W. Knight) working on aspects of the synthesis of Aplasmomycin, an interesting boron containing macrocyclic antibiotic with antimalarial biological activity. Finally at the Dyson Perrins Laboratory at the University of Oxford he worked with Professor Stephen G. Davies on the development of solution- and solid-phase chiral non-racemic auxilaries probing the differences in their asymmetric chemistry on the two-phases. Whilst at Oxford and in conjunction with Yamanouchi Pharmaceuticals he also worked on the development of new medicinal entities with volume regulated chloride channel bioactivity. He took up his current position in the School of Chemistry at UEA in October 2000 and was promoted to Senior Lecturer in 2008.

Selected publications

Sean P. Bew, D. L. Hughes, Nicholas J. Palmer, Vladimir Savic, Katy M. Soapi, Martin A. Wilson.
Stereoselective synthesis of N-alkylaziridines from N-chloroamines.
Chemical Communications, 2006, 33, advanced article
DOI: 10.1039/b608504k

Sean P. Bew, D. L. Hughes, Nicholas J. Palmer, Vladimir Savic, Katy M. Soapi, Martin A. Wilson.
Expedient synthesis of substituted (S)-N-(?)-methylbenzylaziridines.
Chemical Communications, 2006, 33, 3513 - 3515
DOI: 10.1039/b606033a

Sean P. Bew, D. L. Hughes, Sunil V. Sharma.
Acid-catalyzed synthesis of methylene-bridged (S)-tyrosine-phenol dimers.
Journal of Organic Chemistry, 2006, 71, 7881 - 7884.
DOI: 10.1021/jo0610863

 

Academic Background

  • BSc, Chemistry, School of Chemistry, University of Leicester
  • PhD, Organic Chemistry, School of Chemistry, University of Bristol
  • PDRA, Department of Pharmacy and Pharmacology, University of Bath
  • PDRA, School of Chemistry, University of Nottingham,
  • PDRA, School of Chemistry, University of Cardiff,
  • PDRA, Dyson Perrins Laboratory, Oxford University

All Publications

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Bew, S. P., Liddle, J., Hughes, D. L., Pesce, P., Thurston, S. M.

(2017)

Chiral Brønsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl-cis-aziridine Carboxylate Esters,

in Angewandte Chemie International Edition

56

(19)

pp. 5322–5326

Full Text UEA Repository

(Article)

(Published)


Bew, S. P., Stephenson, G. R., Rouden, J., Godemert, J., Seylani, H., Martinez-Lozano, L. A.

(2017)

Gaining insight into reactivity differences between malonic acid half thioester (MAHT) and malonic acid half oxyesters (MAHO),

in Chemistry - A European Journal

23

(19)

pp. 4557–4569

Full Text UEA Repository

(Article)

(Published)


Bew, S. P., Bachera, D. U., Coles, S. J., Hiatt-Gipson, G. D., Pesce, P., Pitak, M., Thurston, S. M., Zdorichenko, V.

(2016)

“Dial Up and Lock In”: Asymmetric organo-Brønsted acid catalysis incorporating stable isotopes,

in Chem

1

(6)

pp. 921–945

Full Text UEA Repository

(Article)

(Published)


Mills, G. P., Hiatt-Gipson, G. D., Bew, S. P., Reeves, C. E.

(2016)

Measurement of isoprene nitrates by GCMS,

in Atmospheric Measurement Techniques

9

(9)

pp. 4533-4545

Full Text UEA Repository

(Article)

(Published)


Bew, S., Hiatt-Gipson, G. D., Mills, G. P., Reeves, C.

(2016)

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate,

in Beilstein Journal of Organic Chemistry

12

pp. 1081-1095

Full Text UEA Repository

(Article)

(Published)


Bew, S. P., Stephenson, G. R., Rouden, J., Ashford, P. A., Bourane, M., Charvet, A., Dalstein, V. M. D., Jauseau, R., Hiatt-Gipson, G. D., Martinez-Lozano, L. A.

(2015)

Bioinspired, base- and metal-free, mild decarboxylative aldol activation of malonic acid half thioesters under phase-transfer reaction conditions,

in Advanced Synthesis & Catalysis

357

(6)

pp. 1245-1257

Full Text UEA Repository

(Article)

(Published)


Anwar, A., Archibald, S., Audisio, D., Badman, G., Bergin, J., Bew, S. P., Bloom, J., Bushby, N., Busigin, A., Chan, M. Y. T., Davies, J., Dilworth, J., Dunscombe, M., Elmore, C. S., Engstrom, P., Fuchter, M. J., Geach, N. J., Georgin, D., Griffiths, A., Hansen, P., Hardcastle, G., Hiatt-Gipson, G. D., Hickey, M. J., Kitson, S. L., Lashford, A., Lenz, E., Lewinton, S., Lockley, W. J. S., Loreau, O., Maddocks, S., Marlière, P., Mcewen, A., Moody, T. S., Morgan, P., Roe, S. J., Schenk, D. J., Speed, D. J., Stockman, R. A., Sumal, K., Taran, F., Thurston, S., Waring, M., Watters., W. H.

(2015)

Abstracts of the 23rd International Isotope Society (UK group) Symposium: Synthesis and applications of labelled compounds 2014,

Full Text

(Other contribution)

(Published)


Bew, S.

(2015)

Method and catalyst for synthesising aziridine,

(Other contribution)

(Published)


Michalska, M., Songis, O., Taillier, C., Bew, S., Dalla, V.

(2014)

Synergistic gold(I)/trimethylsilyl catalysis: Efficient alkynylation of N,O-acetals and related pro-electrophiles,

in Advanced Synthesis & Catalysis

356

(9)

pp. 2040-2050

Full Text UEA Repository

(Article)

(Published)


Bew, S., Stephenson, G., Rouden, J., Martinez-Lozano, L., Seylani, H.

(2013)

Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols,

in Organic Letters

15

(15)

pp. 3805-3807

Full Text UEA Repository

(Article)

(Published)


Bew, S., Ashford, P., Bachera, D.

(2013)

Synthesis of structure and function diverse α-D-diazoacetates, α-D-diazoacetamides, α-D-diazoketones, and the antibiotic α-D-azaserine,

in Synthesis

45

(7)

pp. 903-912

Full Text UEA Repository

(Article)

(Published)


Bew, S., Burrows, A., Düren, T., Mahon, M., Moghadam, P., Sebestyen, V., Thurston, S.

(2012)

Calix[4]arene-based metal-organic frameworks: Towards hierarchically porous materials,

in Chemical communications (Cambridge, England)

48

(40)

pp. 4824-4826

Full Text UEA Repository

(Article)

(Published)


Savjani, N., Bew, S., Hughes, D., Lancaster, S., Bochmann, M.

(2012)

Reactivity of "ligand-free" Au: C-H and C-C activation versus π coordination,

in Organometallics

31

(7)

pp. 2534-2537

Full Text UEA Repository

(Article)

(Published)


Ashford, P., Bew, S.

(2012)

Recent advances in the synthesis of new glycopeptide antibiotics,

in Chemical Society Reviews

41

(3)

pp. 957-978

Full Text UEA Repository

(Article)

(Published)


Bew, S., Hiatt-Gipson, G., Lovell, J., Poullain, C.

(2012)

Mild Reaction Conditions for the Terminal Deuteration of Alkynes,

in Organic Letters

14

(2)

pp. 456-459

Full Text UEA Repository

(Article)

(Published)


Bew, S., Sharma, S.

(2011)

Do commercially available metal salts mediate calixarene formation via hydrogen-bonded dimers?,

in The Journal of Organic Chemistry

76

(17)

pp. 7076-7083

Full Text UEA Repository

(Article)

(Published)


Bew, S., Sharma, S.

(2011)

Controlling Calixarene Size with Metal Salts: The First Brønsted-Free Synthesis,

in Synfacts

2011

(11)

pp. 1188-1188

Full Text UEA Repository

(Article)

(Published)


Savjani, N., Lancaster, S., Bew, S., Hughes, D., Bochmann, M.

(2011)

Synthesis and structures of gold perfluorophthalimido complexes,

in Dalton Transactions

40

(5)

pp. 1079

Full Text UEA Repository

(Article)

(Published)


Bew, S., Hiatt-Gipson, G.

(2010)

Synthesis of C -propargylic esters of N-protected amino acids and peptides,

in The Journal of Organic Chemistry

75

(11)

pp. 3897-3899

Full Text UEA Repository

(Article)

(Published)


Bew, S., Barter, A., Sharma, S.

(2010)

Mass spectroscopic investigation of bis-1,3-urea calix[4]arenes and their ability to complex N-protected α-amino acids,

in Journal of Inclusion Phenomena and Macrocyclic Chemistry

66

(1)

pp. 195-208

Full Text UEA Repository

(Article)

(Published)


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Key Research Interests

Our research interests are broad and have in common the development and application of synthetic organic chemistry for the formation of, quite often, new and unusual chemical entities. To facilitate and enable this process we utilise state-of-the-art chemical techniques, equipment and protocols. One of our aims is to make our chemistry accessible and relatively simple to execute. Furthermore we try and exemplify our reactions using structure and function diverse substrates hopefully demonstrating as broadly as possible the scope of a particular reaction. Where possible we report substrates that have failed to react, this is often useful allowing potential users to gauge if an unknown substrate is likely to work for them.

One particular area of interest to us is the development of new synthetic methodologies that allow the efficient, atom-economic, organocatalytic formation of small strained heterocycles called aziridines. Here we have developed several routes to chiral racemic and chiral non-racemic aziridines. As well as further optimising these towards more diverse substrates our attention is also focused on utilising this methodology for the total synthesis of several natural product derived glycopeptide antibiotics for example vancomycin and analogs of vancomycin. In conjunction with these studies the chemical exploitation of our aziridine methodology for the synthesis of alternative heterocyclic motifs is currently under way as is gaining an in depth understanding of the mechanism associated with the asymmetric synthesis of the aziridines.

A second area of considerable research effort within our group is the efficient construction of calixarenes appended, principally on the upper-rim, with diverse chemical and functional groups. At the core of this is the design and synthesis of new molecular materials, which allow us to explore their properties relating these to their structure. Aspects of this work focus on using supramolecular chemistry and catalysis for the construction of man-made biomachines that mimic, for example, enzymes. Of particular interest to us is the formation of a ‘synthetic’ calixarene-derived polyketide synthase, a very large enzyme that, ordinarily, is used by Nature for secondary metabolite formation.

Our interest in calixarene chemistry has expanded into its potential use as a sensitive sensor for gold. Employing a series of specific transformations we have been able to generate a series of structure and function diverse calixarenes that demonstrate the viability of appending specific chemical handles onto the upper-rim of a calixarene allowing the new species to specifically ‘sense’ gold, even in the presence of contaminating salts from Group 1, 2 or even metals that are chemically very similar to gold, for example platinum and mercury.

Trøgers base is an interesting, readily generated bicyclic heterocycle with a well-defined V-shaped, relatively rigid 90° conformational bias. Albeit it has been known for over 125 years it has only recently been the subject of close scrutiny undergoing chemical manipulation and investigation. We are interested in further extending these studies. Thus we have initiated a research effort that aims to exploit its unusual conformational bias probing its potential in biology and medicinal chemistry, as well as investigating its utility as a conformationally bound linker within supramolecular chemistry.
 

External Activities and Indicators of Esteem

  • EPSRC College Member. June 2013
  • Referee proposals for EPSRC, ACS Petroleum Research Fund, NSF, Leverhulme Trust and A-star.2008 - present
  • Macrocyclic and Supramolecular Chemistry Group committee member. December 2012
  • International invited talk at Calix2011, ICIQ, Tarragona, Spain. June 2011
  • Secretary of the Gregynog Synthesis Society, 2009 - 2011
  • International invited talk at Calix2013, Memorial University of Newfoundland, St Johns, Canada. July, 2013
  • International invited talk at the University of Rouen, France. July, 2011
  • International invited talk at FLOHET 12, Annual Florida Heterocyclic and Synthetic Chemistry Conference, University of Florida, USA. March, 2011
  • International invited talk at Gakushuin University, Tokyo, Japan. June, 2010
  • International invited talk at Keio University, Yokohama, Japan.June, 2010
  • International invited talk at Department of Chemistry, University of Texas at Austin, USA. March, 2010
  • International invited talk at 10th International Calixarene Conference, University of Korea, Seoul, South Korea. July, 2009
  • International invited talk at Kyushu University, Fukuoka, Japan. September 2008
  • International invited talk at Ewha 4th NanBio Symposium, Seoul, South Korea. September 2008
  • Regularly referee manuscripts for I regularly review manuscripts for example: Advanced Synthesis & Catalysis, Arkivoc, Chemical Communications, Chemical Society Reviews, Energy & Environmental Science, European Journal of Organic Chemistry, Journal of the American Chemical Society, Journal of Organic Chemistry, New journal of Chemistry, Organic & Biomolecular Chemistry, Organic Letters, Nature, Nature Chemistry, Synthesis, Synthetic Communications, Tetrahedron, Tetrahedron Letters, Tetrahedron: Asymmetry. 2008 - present

Key Responsibilities

  • School of Chemistry library representative
  • Organic safety officer
  • Chair of mass spectrometry committee

Administrative Posts

  • School of Chemistry library representative
  • Organic safety officer
  • Chair of mass spectrometry committee