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Photo Dr. Peter B. Wyatt,
MA DPhil (Oxon), CSci CChem MRSC

Senior Lecturer in Organic Chemistry

School of Biological & Chemical Sciences
Queen Mary, University of London
Joseph Priestley Building, Mile End Road
London E1 4NS
Tel: +44 (0) 20 7882 3267
Fax: +44 (0) 20 7882 7427
email: P.B.Wyatt@qmul.ac.uk

Research Interests

•  Synthesis of fluorinated organic ligands
•  Optical and electronic properties of metallo-organic materials
•  Synthesis of unusual amino acids
•  Synthesis of organophosphorus compounds
•  Anti-cancer drugs and their metabolites
•  Stereoselective synthesis of C-glycosides
•  Organic electrochemistry

Synthesis of fluorinated organic ligands, optical and electronic properties of metallo-organic materials

In association with colleagues in the School of Physics and Astronomy at Queen Mary we are engaged in the synthesis of new metal complexes for use in the production of optoelectronic devices such as organic light-emitting diodes and low cost optical amplifiers. Recent work has shown that the major obstacle to the use of these materials, the short lifetimes of the lanthanide ions in organic hosts, can be overcome by using highly halogenated ligands (e.g. structures 1 and 2 above). We are combining synthetic chemistry expertise with optical and electrical characterisation of the complexes and the fabrication of devices (refs 1-5).

Synthesis of unusual amino acids

Many amino acids exist in nature beyond the proteinogenic ones that are directly specified in the genetic code. We are working on the chemical synthesis and manipulation of rare amino acids such as oxohistidine (structure 3 above), formed by post-translational protein oxidation, in order to gain a better understanding of Alzheimer's disease and other degenerative conditions (ref. 6).

Synthesis of organophosphorus compounds

In addition to their potential for metal complexation, phosphonic acid derivatives are biologically relevant because of their resemblance to phosphate esters and their ability to mimic the tetrahedral transition state geometry during ester and amide hydrolysis. We have devised an enantioselective synthesis of the amino phosphonic acid 4 above, which is a natural product. The synthetic material produced in our laboratory was recently used in a study of enzyme systems that can metabolise carbon-phosphorus bonds (ref. 7).

Anti-cancer drugs and their metabolites

Reference samples of anti-cancer drug metabolites which we have prepared are used as standards for quantitative analysis of drug metabolism in cancer patients at St Bartholomew's Hospital (ref. 8). We also proposed a chemical mechanism for the inactivation of the anticancer drug bortezomib 5 by the dietary plant polyphenol quercetin 6 (ref. 9).

C-Glycoside synthesis

There is a growing appreciation of the importance of oligosaccharides as recognition elements in biology (e.g. in the processes giving rise to bacterial infection and inflamation). However, natural sugars do not usually make good drugs because sugar-receptor interactions are relatively weak and glycosidic linkage is too easily metabolised. We have devised new chemical methods for the synthesis of stable carbohydrate analogues with metabolically stable carbon-carbon bonds at the so-called anomeric position (e.g. compounds 7 and 8 ) (refs. 10,11).

Organic Electrochemistry

Electrochemistry provides a controlled and environmentally friendly way of adding electrons to organic molecules without generating metal salts as by-products. Reduction of chiral phenazine derivatives such as 9 produces strongly basic radical ions which can be used to bring about the asymmetric ring opening of epoxides (refs.12,13). Recently we contributed a chapter that reviews electrogenerated bases to a major book on organic electrochemistry (ref. 14).

 

Selected Recent Publications

1. Evidence for erbium-erbium energy migration in erbium(III) bis(perfluoro- p -tolyl)phosphinate, R. H. C. Tan, J. M. Pearson, Y. Zheng, P. B. Wyatt and W. P. Gillin, Appl. Phys. Lett ., 2008, 92 , 103303-1 to 103303-3.

2. Near IR luminescent rare earth 3,4,5,6-tetrafluoro-2-nitrophenoxide complexes: synthesis, X-ray crystallography and spectroscopy, Y. Zheng, M. Motevalli, R. H. C. Tan, I. Abrahams, W. P. Gillin and P. B. Wyatt , Polyhedron , 2008, 27 , 1503-1510.

3. Erbium bis(pentafluorophenyl)phosphinate: a new hybrid material with unusually long-lived infrared luminescence, Y. Zheng, J. Pearson, R. H. C. Tan, W. P. Gillin and P. B. Wyatt , J. Mater. Sci: Mater. Electron. 2009, 20 , S430-S434.

4. Nonradiative de-excitation mechanisms in long-lived erbium(III) organic compounds Erx Yx [( p -CF3-C6F4)2 PO2 ]3 , I. Hernández, R. H. C. Tan, J. M. Pearson, P. B. Wyatt and W. P. Gillin, J. Phys. Chem. B , 2009, 113 , 7474-7481.

5. Cooperative infrared to visible up conversion in Tb 3+, Eu 3+ and Yb 3+ containing polymers, I. Hernández, N. Pathumakanthar, P. B. Wyatt and W. P. Gillin, Adv. Mater. , 2010, 22 , 5356-5360.

6. Is oxidation the trigger of the Amyloid Cascade?: A synthesis of 2-oxo-histidine for incorporation into the Amyloid beta sequence, H. M. Wright, P. B. Wyatt and J. H. Viles, J Pept. Sci. , 2010, 16 , 66-66.

7. PhnY and PhnZ Comprise a New Oxidative Pathway for Enzymatic Cleavage of a Carbon-Phosphorus Bond, F. R. McSorley, P. B. Wyatt , A. Martinez, E. F. DeLong, B. Hove-Jensen and D. L. Zechel, J. Am. Chem. Soc. 2012, 134 , 8364-8367.

8. GAMEC a new intensive protocol for untreated poor prognosis and relapsed or refactory germ cell tumours, J. Sharmash, T. Powles, W. Ansell, J. Stebbing, K. Mutsvangwa, P. Wilson, S. Asterling, S. Liu, P. Wyatt , S. P. Joel and R. T. D. Oliver, Br. J. Cancer , 2007, 97 , 308-314.

9. Dietary flavonoids inhibit the anticancer effects of the proteasome inhibitor bortezomib, F-T. Liu, S. G. Agrawal, Z. Movasaghi, P. B. Wyatt , I. U. Rehman, J. G. Gribben, A. C. Newland and L. Jia, Blood , 2008, 112 , 3835-3846.

10. Synthesis of Propargyl C-glycosides using Allenyltributylstannane, K. L. Chan, G. S. Coumbarides, S. Islam and P. B. Wyatt , Tetrahedron Lett. , 2005, 46 , 61-65.

11. Stereoselective synthesis of ( E )-mannosylidene derivatives using the Wittig reaction, G. S. Coumbarides, M. Motevalli, W. A. Muse and P. B. Wyatt, J Org. Chem., 2006, 71 , 7888-7891.

12. Synthesis of phenazine derivatives for use as precursors to electrochemically generated bases, A. Mateo Alonso, R. Horcajada, H. J. Groombridge, R. Chudasama (née Mandalia), M. Motevalli, J. H. P. Utley and P. B. Wyatt , Org. Biomol. Chem., 2005, 3 , 2832-2841.

13. The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation, A. Mateo Alonso, R. Horcajada, M. Motevalli, J. H. P. Utley and P. B. Wyatt , Org. Biomol. Chem., 2005, 3 , 2842-2847.

14. Electrogenerated Bases and Nucleophiles, J. H. P. Utley, M. F. Nielsen and P. B. Wyatt in Organic Electrochemistry, 5th Edition, Ed O. Hammerich and B. Speiser, CRC Press Inc, 2012, Ch 32.


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by P.B.Wyatt. © Queen Mary, University of London 2012
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