Tim BEACON

Dr Juma’a Al-Dulayymi

Organic chemist

chs00c@bangor.ac.uk

Bangor University

I am a Research Teaching Fellow of the University and I have been and remain involved in a number of aspects of research in chemistry and biochemistry that have drawn on my wide expertise in complex, multiple-step organic synthesis. I have an extensive record of peer-reviewed publications covering my specialist fields of which over 85% have been published during my time in Bangor and working in the field of natural products and their derivatives. I am involved with international programmes of research directly related to the treatment of tuberculosis and asthma involving collaborative work with research groups in Belgium, Germany and South Africa as well as UK based research groups and companies. As part of this on-going and internationally respected work, our research group at Bangor has synthesised key components in the cell wall of the causative factor of TB, Mycobacterium tuberculosis. Other work was involved the isolation and modification of saponins isolated from indigenous Welsh plants.

Research Interests

• Organic synthesis of novel compounds
• De novo synthesis of natural products
• Modification of natural products by organic synthesis to increase action or efficacy
• Handling of unstable natural and synthetic compounds
• Use of spectroscopic methods to identify the structure of novel compounds
• Various chromatographic separation techniques at analytical and preparatives

Background

1981 :  M.Sc. in Organic Chemistry, Baghdad, Iraq.
1991:  Ph.D. in Chemistry, University of Newcastle Upon Tyne., UK

BEACON Activities

The group is focused on 3 key activities: the identification of new natural products from local plants, their use in the synthesis of high value (natural or semi-synthetic) compounds and the development of novel products using silica or boron.

P1- Extraction of actives from local Squill varieties.
P2- Semi-synthesis of brassinolides and analogues
P3- Development of new silicic-boron foliar materials.

Future Plans

• Establish a platform for silicic and boron materials
• Expand the synthesis of high value (natural or semi-synthetic) compounds

Publications

1.  Reaction of 2 aminobenzthiazole and 3 amino 5 methylisoxazole with isothiocyanates. H.H.Al Nima, Juma’a R. Al Dulayymi and O.K.Hashim, J. Iraqi. Chem. Soc., 1986, 11,13.

2.  A novel method for the preparation of β,γ  unsaturated carbonyl compounds.A. Khalaf, Juma’a R. Al Dulayymi, M.S.Mustaffa, J.H.Ali and A.K.Hasheem, J.Iraqi.  Chem. Soc. 1988,13:1, 159 172.

3.  Highly functionalised carbenes and cyclopropenes from tetrahalocyclopropanes. Juma’a R. Al Dulayymi and M.S.Baird.  Tetrahedron Letts., 1988, 6147.

4.  The stereoselectivity of ring opening of 3 substituted cyclopropenes and intermolecular trapping of derived vinyl carbenes. Juma’a R. Al Dulayymi, M.S.Baird and W.Clegg. Tetrahedron Letts., 1988, 6149.

5.  A novel route to optically active dihydropyrans and 3 methylenetetrahydrofurans. Juma’a R. Al Dulayymi and M.S.Baird,  Tetrahedron Letts., 1989, 253.

6.  Substituent effects in the generation and trapping of 1,2 dichloro 3,3 dialkylbut 2 en1 ylidenes.  Juma’a R. Al Dulayymi, M.S.Baird and H.H.Hussain, Tetrahedron Letts., 1989, 2009, 4.

7.  A highly stereoselective generation and trapping of 1,2 dichloro 3 methyl 4 phenylbut 2 enylidenes. Juma’a R. Al Dulayymi, M.S.Baird and W.Clegg.  J.Chem.Soc., Perkin Trans. 1989, (1), 1799.

8.  Generation and trapping of vinylcarbenes at ambient temperatures: a route to functionalised vinyl and allylidenecyclopropanes. Juma’a R. Al Dulayymi and M.S.Baird. Tetrahedron, 1989, 7601.

9.  Optically active dihydropyrans and 3 methylenetetrahydrofurans from cyclopropenyl ethanol derivatives. Juma’a R. Al Dulayymi and M.S.Baird, Tetrahedron, 1990, 5703.

10. Synthetic and mechanistic aspects of the cyclopropenes to vinylcarbene rearrangement. Juma’a R. Al Dulayymi, M.S.Baird and H.H.Hussain. Strain and its implications in Organic Chemistry, 1989, 117 120.

11. Synthesis of 1 chloro 2 vinyl 1H phosphirenes by trapping of vinylcarbenes with phosphaalkynes. H. Memmesheimer, Juma’a R. Al Dulayymi, M.S.Baird, T.Wetting and M.Regitz, Syn. Lett, 1991, 433.

12. An  unusual anion promoted hydrogen shift. Juma’a R. Al Dulayymi and M.S.Baird, Tetrahedron Letts., 1992, 835.

13. An unusual example of stereoelectronic control in the ring opening of 3,3 disubstituted 1,2 dichloro cyclopropene. M.S.Baird, Juma’a R. Al Dulayymi, H.Rzepa and V.Thoss. J.Chem.Soc., Chem. Comms, 1992, 1323.

14. The stereochemistry of ring opening of 3 alkyl 1,1 dihalocyclopropenes to vinyl carbenes at ambient temperature. Juma’a R. Al Dulayymi, M.S.Baird and H.L.Fitton.  Tetrahedron Letts., 1992, 4803.

15.  Degradation studies under neutral and basic condition on Ciprofibrate, an orally active hypolipidemic agent containing a (4 alkoxyaryl) 1 1 dichlorocyclopropane unit. Juma’a, R. Al Dulayymi, M.S.Baird, S.J.Byard, G.Carr, G.J.Ellames, J.W.Firth, J.M.Herbert, M.A.Donald, P.R.Vojvodic and L.M.Wrench., J.Chem.Soc., Perkin Trans. II 1993, 43.

16.  A 1,2   silicon shift in cyclopropylidenes leading to 1 trialkylcyclopropenes M.S.Baird, C.M.Dale and Juma’a R. Al Dulayymi, J.Chem.Soc., Perkin Trans. I, 1993, 1373.

17. Highly functionalised methylenecyclopropanes from cyclopropenes. M.S.Baird, M.F. Shortt , H.H.Hussain and Juma’a R. Al Dulayymi, J.Chem.Soc., Perkin Trans. I, 1993, 1945.

18.  Unusual chemo and stereo selectivities in the reactions of 1,2 dichlorocyclopropenes with nitrile oxides, M.S.Baird, X. Li, Juma’a R. Al Dulayymi, A.I.Kurdjukov and V.A.Pavlov, J.Chem.Soc., Perkin Trans. I, 1993, 2507.

19. 1,2 dibromoalk 2 enylidenes by ring opening of 1,2 dibromo 3 alkylcyclopropenes at ambient temperatures, Juma’a R. Al Dulayymi, M.S.Baird , H. L.Fitton and L.Rajaram. J.Chem.Soc., Perkin Trans. I, 1994, 1633.

20. The stereochemistry of a cyclopropene vinyl carbene rearrangement. Juma’a R. Al Dulayymi, M.S.Baird, L.Rajaram and W.Clegg. J. Chem. Res. (S), 1994, 344.

21. A direct and a formal trapping of propa 1,2 dienylidene. Juma’a R. Al Dulayymi and M.S.Baird. Tetrahedron Letts., 1995, 3393.

22. A generation and trapping of 1,2 Dibromo 3 methyl but 2 en 1 ylidenes. A.R.Al Dulayymi, Juma’a R. Al Dulayymi, M.S.Baird and L.Rajaram. Tetrahedron, 1995, 8371.

23. 1,2,2 tribromocyclopropanecarboxylic acid and derivatives valuable intermediates for Foure carbon cyclopropane and cyclopropene synthons. Juma’a R. Al Dulayymi, A.R.Al Dulayymi, M.S.Baird, S.D.Harkins, E.Roberts and G.Koza. Tetrahedron, 1996, 3409.

24.  Dipolar cycloaddition of a phosphorynitrile oxide to functionalised cyclopropenes. Juma’a R. Al Dulayymi, M.S.Baird, V.A.Pavlov and A.I.Kurdjukov. Tetrahedron, 1996, 8877.

25.  Stucture based interference with insect behaviour cyclopropene analogues of pheromones containing Z alkenes, Juma’a R. Al Dulayymi, M.S.Baird, M.J.Simpson, S.Nyman and G.R.Port. Tetrahedron, 1996,12509.

26. Synthesis of inhibitors of fatty acid desaturases. Juma’a R. Al Dulayymi, M.S.Baird, C.M.Dale, B.Greham, M.Shortt and M.J.Simpson. Synthesis in Lipid Chemistry, 1996, 1-14.

27. A simple and efficient hydrodehalogenation of 1,1-dihalocyclopropanes. Juma’a R. Al-Dulayymi, M.S.Baird, I.G.Bolesov, V.Tveresovsky and M.Rubin, Tetrahedron Letts., 1996, 8933.

28.  Synthesis of putative Δ6- , Δ12- and Δ15- desaturase inhibitors. J.R.Al Dulayymi, M.S.Baird, C.M.Dale, B.Greham and M.F.Shortt. Tetrahedron, 1997, 1099.

29.  Simple Four and Five Carbon Cyclopropane Synthesis Intermediates. Juma’a R. Al-Dulayymi, A.R.Al-Dulayymi, M.S. Baird and G. Goza. Journal of Organic Chemistry USSR, 1997, 33, 867.

30.  A flexible route to [4.1.1] propellanes. A.R.Al-Dulayymi, Juma’a R.Al-Dulayymi and M.S.Baird. Tetrahedron Letts,. 1997, 6755.

31. The synthesis of both enatiomers of lactobaccilic acid and mycolic acids analogues. G.Coxon, S.Knobl, E.Roberts, M.S.Baird, Juma’a  R. Al-Dulayymi, G.S.Besra, P.J.Brennan, and D.E.Minnikin, Tetrahedron Letts., 1999, 6689.

32.  A flexible route to [4.1.1] propellane; A.R.Al-Dulayymi, Juma’a R. Al-Dulayymi and M.S.Baird. Tetrahedron, 2000, 1115.

33. The cycloaddition of cyloproprenes to enones. Juma’a R. Al-Dulayymi, M.S.Baird, H.H.Hussain, B.J.Alhourani, A.Y.Alhabashna, S.J.Coles and M.B.Hursthouse, Tetrahedron Letts., 2000, 4205.

34.   The hydrodehalogenation of 1,1-dibromocyclopropanes by Grignard reagents promoted by titanium compounds. Juma’a R. Al-Dulayymi, M.S.Baird, I.G.Bolesov, V.Tveresovsky and AV.Nizovtsev, J. Chem. Soc.Perkins Trans 2, 2000,1603.

35.  The synthesis of single enantiomers of meromycolic acid. Juma’a R. Al-Dulayymi, M.S.Baird and E.Roberts, Tetrahedron Letts., 2000, 7107.

36.  Salicylate 5-hydroxylase from Ralstonia spp. Strain U2: a monooxygenase with close relationships to and Shard electron transport proteins with naphthalene dioxygenase. N. Zhou, Juma’a R. Al-Dulayymi, M.S.Baird and P.Williams. Journal of Bacteriology, 2002.1547.

37.  Accumulation of 2-aminophenoxazin-3-one-7-carboxylate during growth of Pseudomonas Putida TW3 on 4-hydroxyaminobanzoate lyase (PnbB). M.A.Hughes, M.J.Baggs, Juma’a R Al-Dulayymi, M.S.Baird and P.Willams. Applied and Enviromental Microbiology,  2002, 4965.

38. The synthesis of a single enantiomer of a major a-mycolic acid of Mycobacterium tuberculosis, Juma’a R Al-Dulayymi, M.S.Baird and E.Roberts, J. Chem. Soc.,  Chemical. Communications, 2003, 228.

39. Effective and selective mild catalytic hydrodehalogenation of halocyclopropanes:  preparative capabilities and mechanistic aspects; A. Nizovtesv, Juma’a R. Al-Dulayymi, M.S.Baird, I.G.Bolesov and V.V.Tverezovski. Kinetics and Catalysis, 2003, 44:2.

40. The synthesis of (11R, 12S)-Lactobacillic and its enantiomer: G.D.Coxon, Juma’a R. Al-Dulayymi, M.S.Baird, S.Knobl, E.Roberts and D.E.Minnikin, Tetrahedron: Asymmetry, 2003,14, 1211.

41.  The absolute stereochemistry of grenadamide: Juma’a R. Al-Dulayymi, M.S.Baird and K.Jones, Tetrahedron, 2004, 60, 341.

42.  Synthesis and properties of methyl 5-(1' R, 2'S)-(2-octadecylcycloprop-1-yl) pentanoate and other ω-19 chiral cyclopropane fatty acids and esters related to mycobacterial mycolic acids. G.D.Coxon, Juma’a R. Al-Dulayymi, C.Morehouse, P.J.Brennan, G.S.Besra, M.S.Baird, and D.E.Minnikin. Chemistry and Physics of Lipids, 2004, 127, 35.

43.  The synthesis of a single enantiomer of a major a-mycolic acid of Mycobacterium tuberculosis. Juma’a R. Al-Dulayymi, M.S.Baird and E.Roberts, Tetrahedron, 2005, 61, 11939.

44. The synthesis of one enantiomer of the α-methyl-trans-cyclopropane unit of mycolic  acids, Juma’a R. Al-Dulayymi, M.S.Baird, H.M.Mohammed, E.Roberts and W.Clegg. Tetrahedron, 2006, 62, 4851.

45. The synthesis of a single enantiomers of meromycolic acids from mycobacterial wax esters., Juma’a R. Al-Dulayymi, M.S.Baird, E.Roberts and D. E. Minnikin. Tetrahedron, 2006, 62, 11867.

46. The first synthesis of  single enantiomers of the major methoxymycolic acid  of Mycobacterium tuberculosis, Juma’a R. Al-Dulayymi, M.S.Baird, E.Roberts, M.Dreysel and J.Verschoor. Tetrahedron,  2007, 63, 2571,

47. The first unique synthetic mycobacterial cord factor, Juma’a R. Al-Dulayymi, Maximiliano Maza-Iglesias, M.S.Baird, Seppe Vander Beken and John Grooten; Tetrahedron Letts., 2009, 50, 3702.
     
48. The first synthesis of single enantiomers of the keto mycolic acids, G. Koza, C. Theunissen,  Juma’a R. Al-Dulayymi and Mark S. Baird. Tetrahedron, 2009, 65, 10214.

49. The synthesis of a single enantiomers of protected trans-alkene containing mycolic acid, G. Koza, R. Rowles, C. Theunissen, Juma’a R. Al-Dulayymi and Mark S. Baird, Tetrahedron Letts., 2009, 50, 7259.

50.  The first synthesis of epoxy-mycolic acids,  Dakhil Z. Al-Kremawi, Juma’a R. Al-Dulayymi and Mark S. Baird. Tetrahedron Letts., 2010, 51, 1698.

51. Molecular structure of the Mycobacterium tuberculosis virulence factor,  mycolic acid, determines the elicited inflammatory pattern., S.V.Beken, Juma’a R. Al-Dulayymi, T.rt, T.Naessens, G.Koza, M.M.Iglesisa, R. Rowles, C.Theunissen, J. De Medts, E.Lanckacker, M.S.Baird and J.Grooten; European Journal of Immunology, 2011, 41, 450.

52.  The synthesis of a major α’-mycolic acid of Mycobacterium smegmatis, Maged Muzael, Gani Koza, Juma’a R Al Dulayymi, Mark S. Baird, Chemistry and Physics of Lipids, 2010, 163, 678.
    
53.  Structure-function relationships of the antigenicity of mycolic acids in tuberculosis patients, M. Beukes, Y. Lemmer, M. Deysel, Juma’a R. Al-Dulayymi, M. S. Baird, G. Koza, M. M. Iglesisa, R. R. Rowles, C. Theunissen, J. Grooten, G. Toschi, V.V. Roberts, L. Pilcher, S. V. Wyngaardt, N. Mathebula, M. Balogun, A. C. Stoltz and J. Verschoor, Chemistry and Physics of Lipids, 2010, 163, 800.
 
54.  Diastereomeric cyclic tris-allenes, Hussain H. Mustafa, Mark S. Baird, Juma’a R. Al-Dulayymi and V. V. Tverezovskiy; J. Chemical Society, Chem. Commun.,  2013, 49, 2497.

55. Thiol modified Mycolic acids, M. M. Balogun, E. H. Huws, M. M. Sirhan, A. D. Saleh, Juma’a R. Al-Dulayymi, L. Pilcher, J. A. Verschoor and Mark S. Baird;  Chemistry and Physics of Lipids, 2013, 172-173, 40-57.

56. The synthesis of methoxy and keto mycolic containing methyl-trans-cyclopropanes, G. Koza, M. Muzael, R. R. Schubert-Rowles, C. Theunissen, Juma’a R. Al-Dulayymi and Mark S. Baird; Tetrahedron, 2013, 69, 6285.

57. Tandem rearrangements of a cyclic bis-allene, Hussain H. Mustafa, Mark S. Baird, Juma’a R. Al-Dulayymi and V. V. Tverezovskiy; Tetrahedron, 2014, 70, 1502.

58.  A nine carbon homologating system for skip-conjugated polyenes, Hussain H. Mustafa, Mark S. Baird, Juma’a R. Al-Dulayymi and V. V. Tverezovskiy; Chemistry and Physics of Lipids, 2014, 183, 34-42.

59.  Synthetic epoxy-mycolic acids, Dakhil Z. Al-Kremawi, Juma’a R. Al-Dulayymi and Mark S. Baird. Tetrahedron, 2014, 70, 7322

60.  Synthetic trehalose di- and mono-ester of α-, Methoxy-, and Keto-mycolic acids, Juma’a R. Al-Dulayymi, Maximiliano Maza-Iglesias, M.S.Baird, Rwoa’a T. Hameed, Klarah S. Baols, Majed Muzael, and Ahmad D. Saleh; Tetrahedron, 2014, 70, 9836.

61. Mycolyl arabino glycerols from synthetic mycolic acid, M. O. Mohammed, Mark S. Baird and Juma’a R. Al Dulayymi; Tetrahedron Lett., 2015, 56, 3268.

62. Synthetic trehalose esters of cis-alkene and diene α’-mycolic acids of Mycobacteria, S. G. Taher, M. Muzael, Juma’a R. Al Dulayymi and Mark S. Baird; Chemistry and Physics of Lipids, 2015, 189, 28.

63. Synthesis of glucose monomycolates based on single synthetic mycolic acids, M. M. Sahb, Juma’a R. Al Dulayymi and Mark S. Baird; Chemistry and Physics of Lipids, 2015, 190, 9.