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Dr William Martin

PositionLecturer in Chemistry
LocationJ4, Richmond building
DepartmentSchool of Chemistry and Biosciences
Telephone+44 (0) 1274 233362
EmailW.Martin@bradford.ac.uk

Research Interests (key words only)

Organic Synthesis, Natural Product Synthesis, Developing Novel Reactions, Mass Spectrometry, Analysis and Synthesis of Archaeologically important bio-markers

PhD Supervision

Miss Aime Saidykhan, third year

Teaching and Supervisory Responsibilities

  • Stage 1 Organic Chemistry
  • Stage 2 Stereochemistry
  • Stage 2 Labs
  • Stage 3 Organometallic Chemistry
  • Stage 3 Labs

Administrative Responsibilities

  • Stage 3 tutor
  • Placements tutor
  • Organic Chemistry curriculum development

Biography

  • MChem, 2001, University of Nottingham
  • PhD, 2005, University of Nottingham (with Dr Paul Clarke) – Development of the Maitland Japp reaction

Professional History

Postdoctoral fellow 2005, Technical University of Berlin (With Professor Siegfried Blechert) Development of novel gold catalysed reactions

Postdoctoral fellow 2006-2007, Oregon Stage University (With Professor James White) Total synthesis of Solandelactones E and F, synthetic studies tpwards pillaromycinone

Research Areas

In collaboration with Dr Richard Bowen.

Our research is centred on synthetic organic chemistry and mass spectrometry. We enjoy coming up with new ways of making important molecules, and synthesising molecules that are of use in the application of organic chemistry to related sciences. A selection of our current projects are given below. In the School of Chemistry and Biosciences at Bradford we have a strong tradition of getting our undergraduates in to the laboratory and getting them involved in our research. Undergraduate contributions to the projects below are marked with an asterisk.

Synthesis and analysis of biomarkers of archaeological importance

With: Rhea Brettell1, Chloe Townley2*, Richard Gallagher3, Carl Heron1, and Ben Stern1.

1 - School of Archaeological and Forensic Sciences, 2 - School of Chemistry and Biosciences, 3 - AstraZeneca

Support from: AHRS, BMSS, AstraZeneca

Compounds derived from plants can act as useful biomarkers in the archaeological record. For example, resins are known to have been used as part of mortuary rites in the Roman period, and their detection can allow the botanical and geographical source of these highly valued aromatic substances to be elucidated. This has enabled the extent of ancient trade networks and cultural influences to be evaluated. Two such compounds are the isomeric triterpenoids oleanolic acid (1) and ursolic acid (3), both of which can be found in nature as either their 3α (2 and 4) or 3β-epimers.

Synthesis and Analysis

L‌eft: Artist's impression of the Eagle Hotel focal burial, Winchester © Winchester Museums; right: The compounds of interest.

Our colleagues in the School of Archaeological and Forensic Sciences required analytical standards in order to determine the GCMS retention time of these closely related compounds. The synthesis of both epi-isomers of oleanolic and ursolic acid in our laboratory allowed this objective to be achieved, and permitted these compounds to be unambiguously identified.

The mass spectrometry of these, and closely related, compounds has also been studied. We have found that Atmospheric Pressure Chemical Ionisation Mass Spectrometry allows for the stereochemistry at the C-3 alcohol to be accurately determined. This technique will allow these compounds to be identified without having to rely on analytical standards.

For further information see:
Chloe Townley, Rhea C. Brettell, Richard D. Bowen, Richard T. Gallagher, and William H. C. Martin, European Journal of Mass Spectrometry, in press.

Chemistry in a mass spectrometer

Skatole With: Amie Saidykhan1, Stephen Ayrton1*, and Richard Gallagher2.

1 - School of Chemistry and Biosciences, 2 - AstraZeneca

Support from: BMSS, AstraZeneca

‌Mass spectrometry is a fundamental technique for detecting and analysing organic molecules. Recently, it has been realised that chemical reactions can take place under the conditions found in certain mass spectrometry instruments. We became interested in this area when we attempted to analyse indoles such as skatole, 5. The acid catalysed dimerisation of indole is a well-known reaction, but the 'dimerisation' we see in the APCI instrument corresponds to an oxidative process, which is normally radically initiated.

Mass Spec We have deduced that the chemistry is occurring in the nebuliser of the instrument, where small droplets of the effluent from the chromatography column containing the analyte are formed. Nebulisers are familiar in devices such an asthma inhaler, for example. The photo to the left shows an experiment where the analyte was passed through the isolated nebuliser and the spray was then collected and analysed. The reaction is seen in several related indole compounds; it occurs in high conversion under very mild conditions. Current work is aimed at determining the exact mechanism of the reaction, and gauging its synthetic utility.

For further information see:
Amie Saidykhan, Stephen T. Ayrton, Richard T. Gallagher, William H. C. Martin and Richard D. Bowen; Rapid Communications in Mass Spectrometry, 28, pages 1948–1952, 2014.

Rearrangement chemistry of sulphonamides

With: Evelyne Rushingwa 1*, Amie Saidykhan1, Hadi Touray1*, and Richard Gallagher2.

1 - School of Chemistry and Biosciences, 2 - AstraZeneca

Support from: AstraZeneca

The sulphonamide functional group, which is found in a number important medicinal compounds, is widely used in synthetic chemistry. We have been exploring the rearrangement chemistry that occurs when molecules containing a sulphonamide group are treated with a strong base. The molecules that result constitute important classes of biologically active compounds, such as nicotinic acids and saccharines.

William Martin research (Nicotine)

We are also interested in the rearrangement chemistry of amino acid derivatives that contain a sulphonamide functionality. By carefully selecting the reaction conditions we can gain access to α,β-unsaturated systems such as 11, which are important precursors to biologically active systems, or unnatural amino acids such as 12.

William Martin research (pyrimidine)

‌For further information see:

  • Evelyne Rushingwa, Hadijatou K. Touray, Richard D. Bowen, Richard T. Gallagher, William H.C. Martin; Tetrahedron Letters, 54, pages 4726-4728, 2013
  • Amie Saidykhan, Richard D. Bowen, Richard T. Gallagher, William H.C. Martin; Tetrahedron Letters, 56, pages 66-68, 2015

Research Collaborations

Dr Richard Gallagher, Associate Principle Scientist at AstraZeneca

Publications

Townley, C, Brettell, R. C., Bowen R.D., Gallagher, R. T., Martin, W. H. C., The Application of Positive Mode Atmospheric Chemical Ionisation to distinguish Epimeric Oleanolic and Ursolic Acids and related Pentacyclic Triterpenoids, European Journal of Mass Spectrometry, 2015 (in Press)

Saidykhan, A., Bowen R.D., Gallagher, R. T., Martin, W. H. C., "Unexpected rearrangement reactions in tosyl protected amines," Tetrahedron Letters, 2015, 56, 66

Saidykhan, A., Ayrton, S. T., Gallagher, R. T., Martin, W. H. C., Bowen R.D., "Novel formation of [2M–H]+ species in positive electrospray mass spectra of indoles" Rapid Communications in Mass Spectrometry, 2014, 28, 1948

Ayrton, S. T., Panova, J., Gallagher, R. T., Martin, W. H. C., Bowen R.D., "Mass spectra of halogenostyrylbenzoxazoles" International Journal of Mass Spectrometry, 2013, 345, 120

Rushingwa, E., Touray, H., Bowen R.D., Gallagher, R. T., Martin, W. H. C., "Novel nitrogen to carbon rearrangement forming nicotinic acid Sulphonamides" Tetrahedron Letters, 2013, 54, 4726

White, J. D.; Demnitz, F. W. J.; Xu, Q.; Martin, W. H. C., "Synthesis of an Advanced Intermediate for (+)-Pillaromycinone. Staunton−Weinreb Annulation Revisited" Org. Lett., 2008, 10, 2833

White, J. D.; Licoln, C. M.; Yang, J.; Martin, W. H. C.; Chan, D. B., "Total Synthesis of Solandelactones A, B, E, and F Exploiting a Tandem Petasis−Claisen Lactonization Strategy" J. Org. Chem., 2008, 73, 4139

White, J. D.; Martin, W. H. C.; Lincoln, C.; Yang, "Total Synthesis of Solandelactones E and F, Homoeicosanoids from the Hydroid Solanderia secunda," J. Org. Lett., 2007, 9, 3481

Clarke, P. A.; Santos, S.; Martin, W. H. C. "Combining Pot, Atom and Step Economy (PASE) in Organic Synthesis: Synthesis of Tetrahydropyrans" Green Chem., 2007, 9, 438

Martin, W. H. C.; Blechert, S. Curr., "The synthesis of biologically interesting molecules using olefin metathesis" Top. Med. Chem. 2005, 5, 1521

Clarke, P. A.; Martin, W. H. C.; Hargreaves, J. M.; Wilson, C.; Blake, A., "Revisiting the Maitland-Japp Reaction. The One Pot Multicomponent Construction of Highly Substituted Tetrahydropyran-4-ones." J. Org. Biomol. Chem., 2005, 3, 3551

Clarke, P. A.; Martin, W. H. C., "Exploiting the Maitland-Japp Reaction: A Synthesis of (±)-Centrolobine." Tetrahedron, 2005, 61, 5433

Clarke, P. A.; Martin, W. H. C.; Hargreaves, J. M.; Wilson, C.; Blake, A., "Revisiting the Maitland-Japp Reaction. Concise construction of highly functionalised tetrahydropyran-4-ones."  J. Chem. Comm., 2005, 20, 1061

Clarke, P. A.; Martin, W. H. C., "An expedient synthesis of (±)-centrolobine." Tetrahedron Lett, 2004, 45, 9061

Clarke, P. A.; Martin, W. H. C., "Synthetic Methods Part (v): Protecting Groups." Annu. Rep. Prog. Chem., Sect. B, 2003, 99, 84

Clarke, P. A.; Martin, W. H. C. "Diastereoselective Synthesis of Highly Substituted Tetrahydropyran-4-ones." Org. Lett., 2002, 4, 4527

 

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