Al-Dulayymi, Juma - Bangor University

个人简介

My research activity is focused on the synthesis of individual synthetic mycolic acids and their sugar esters, and in collaboration with other groups examining their biological activity. I am also interested in the synthesis of cyclopropenes and their applications and the identification, isolation and modification of natural products from plants.

研究领域

Mycolic acids are long-chain (C70-90) alpha-alkyl beta-hydroxy fatty acids, which form the characteristic components of the cell walls of bacteria such as Mycobacterium tuberculosis and Mycobacterium leprae, which cause two of the most significant diseases known to mankind. They are also present in a range of common environmental mycobacteria and some related species. The presence of mycolic acids in the cell wall of Mycobacterium tuberculosis is believed to be important to the resistance of the cells to many drugs. The most important mycolic acids contain a number of functional groups including one or more cis-cyclopropanes and methyl-trans-cyclopropanes as components of the long chain, and Mycobacterium tuberculosis produces three main classes of mycolic acids: alpha, methoxy (1) and keto. I have been involved in developing the first total synthesis of single enantiomers of the major classes of these mycolic acids, as well as others present in other mycobacteria. I was also involved with the development of the first synthetic cord factors (trehalose esters) e.g. (2), containing complete mycolic acids, as well as other sugar esters e.g. glucose, glycerol and arabinose esters and are working towards the synthesis of tri-arabino di-mycolates and penta-arabino tetra-mycolates. Working in collaboration with other groups, in Bangor and South Africa, the possible use of the above compounds as antigens for the detection of antibodies generated by infection with TB is being investigated. In addition, in collaboration with other groups in Ghent and Southampton the effects of individual mycolic acids and their sugar esters on various cytokines and chemokines in the immune system is also being investigated. This work is targeted towards the treatment of diseases such as asthma and for the identification of new adjuvants. Cyclopropanes are very widely used in synthesis, however the use of cyclopropenes is much less common. I have been involved in the development of efficient routes to cyclopropenes and simple chiral methylenecyclopropanes, which can be used as precursors to biologically active cyclopropanes. Cyclopropenes provide a versatile route to cyclopropanes by inter- or intramolecular addition to the cyclopropene bond, and in the presence of chiral control this can lead to an improved enantiomeric excess in the product cyclopropanes compared to other routes. The use of both of these as precursors of important cyclopropane-containing natural products such as 1-aminocyclopropanecarboxylic acids (growth regulators), methanoproline (controls hypertension), and 1-hydroxycyclopropane carboxylic acids (enzyme inhibitors) is being examined. Methylenecyclopropanes can also serve as useful intermediates in the preparation of optically active heterocycles. Routes to cyclopropene fatty acids, some of which are also present in natural oils, and which show important effects in biological systems have also been developed. We are also working on the synthesis of cyclopropene analogues of pheromones containing Z-alkenes. Indigenous plants provide a rich source of organic molecules that show strong biological properties and can in principle be used to replace petrochemically derived molecules for application in a number of areas such as cosmetics, human and animal health as well as in agriculture. Work in this area has involved the identification of sources of molecules that are effective in the control of potato blight and that control a range of fungi, and by modification of such natural materials the biological activity of such molecules can be changed for a particular beneficial effect. In collaboration with other groups work has been carried out to test the biological activity of the compounds produced against various bacteria and fungi.

近期论文

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68. The synthesis of a single enantiomers of trans-alkene containing mycolic acid, G. Koza, H. M. Ali, R. T. Hameed, R. Rowles, Carys Davies, Juma’a R. Al Dulayymi, C.D. Gwenin and Mark S. Baird; Tetrahedron, 2016 in press 67. Standardization of natural mycolic acid antigen composition and production for use in biomarker antibody detection to diagnose active tuberculosis, F.L. Ndlandla, V. Ejoh, A.C.Stoltz, B. Naicker, A.D. Cromarty, S. van Wyngaardt, M. Khati, L.S. Rotherham, Y. Lemmer, J. Niebuhr, C.R. Baumeister, Jumaa R. Al Dulayymi, H. Swai, M.S. Baird and J.A. Verschoor; Journal of Immunological Methods, 2016, 435, 50-59. 66. Sterculic acid and its analogues are potent inhibitors of Toxoplasma gondii, P. Hao, I. Q. M. Alaragi, Juma’a R. Al Dulayymi, M. S. Baird, J. Liu and Q. Liu; Korean J Parasitol, 2016, 54, 139. 65. Synthesis of Wax esters and related sugar esters from Mycobacterium avium and other mycobacteria, S. G. Taher, Juma’a R. Al Dulayymi, A. Jones, H. M. Ali, Mark S. Baird, Tetrahedron; 2016, 72, 3863 64. Arabino Mycolates from Synthetic Mycolic acids, M. Mohammed, Mark S. Baird, Juma’a R. Al Dulayymi, A. Jones and C.D. Gwenin; Tetrahedron, 2016 ,72, 2849 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 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 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 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. 59. Synthetic epoxy-mycolic acids, Dakhil Z. Al-Kremawi, Juma’a R. Al-Dulayymi and Mark S. Baird. Tetrahedron, 2014, 70, 7322 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. 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. 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. 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. 54. Diastereomeric cyclic tris-allenes, Hussain H. Mustafa, Mark S. Baird, Juma’a R. Al-Dulayymi and V. V. Tverezovskiy; J. Chemical Socity, Chem. Commun., 2013, 49, 2497. 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. 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. 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. 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. 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, 65, 7259. 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. 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 Letters, 2009, 50, 3702. 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, 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. 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.