Baird, Mark S - Bangor University

个人简介

My research activity is focused on the development of new reactions of small ring compounds which have applications in synthesis, and in an examination of their mechanisms using spectroscopic and labelling techniques.

研究领域

Synthesis of Mycolic Acids and other Natural Cyclopropane Fatty Acids (Dr. J. R. Al Dulayymi, D. Al Kremawi, E.Huws, A.Jones, I.Jones, C. Don Lawson, R.Hameed, M.Muzael, A.Saleh, M.Sirhan) Mycolic acids form 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. These acids are thought to be important in controlling the lack of permeability of the cell wall and therefore the resistance of the cells to many drugs. Some of their derivatives show have very strong effects on the immune system. The most important mycolic acids contain a number of functional groups including one or more cis-cyclopropanes and methyl-trans-cyclopropanes as components of a very long chain of carbon atoms (70-90). Little is known about the stereochemistry of these molecules such as (1). The group has completed the first total synthesis of single enantiomers of the major classes of mycolic acid present in a number of mycobacteria, and helped to establish the absolute stereochemistry of the natural molecules. We have developed the first synthetic ‘cord factors’ (trehalose esters) containing complete mycolic acids, such as (2). Working in collaboration with other groups in Bangor and with a group in South Africa, we are examining the possible use of such compounds as antigens to antibodies generated on infection with diseases such as TB, for application in the early detection of disease. Working in collaboration with a group in Ghent, we are examining the specific effects of individual synthetic mycolic acids on various cytokines and chemokines in the immune system. This is targeted to the treatment of immune system diseases such as asthma and to the identification of new adjuvants. Cyclopropenes and Methylenecyclopropanes as Precursors of Biologically Active Cyclopropanes (Dr J.R. Al Dulayymi, E.Huws) Although cyclopropanes are very widely used in synthesis, uses of cyclopropenes are much less common. We have developed efficient routes to a range of cyclopropenes and are now examining their applications. Inter- or intramolecular addition to the cyclopropene bond provides a versatile route to cyclopropanes. We have shown that, in the presence of a chiral control element, this can lead to better enantiomeric excesses in product cyclopropanes than can be obtained by many other routes. We have also developed routes to simple chiral methylenecyclopropanes. The use of cyclopropenes and methylenecyclopropanes 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, and this is being applied to the synthesis of, e.g. optically active alkaloids. Other cyclopropane fatty acids are present in a range of natural oils. Again the group is seeking to establish a complete picture of their absolute stereochemistry in order to understand their biosynthesis. We have also developed routes to cyclopropene fatty acids, some of which are also present in natural oils, and which show important effects in biological systems. Identification and Isolation of Bioactive Plant Lipids (N. Ahmed) 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 such as fungicides for application in human and animal health as well as in agriculture. The group has identified sources of molecules that are effective in the control of potato blight, that control a range of fungi, and that can be used to control infestations of molluscs. By chemical modification of the natural materials we can tune the bioactivity to a particular beneficial effect and try to control any adverse effects. Other plants provide rich sources of novel fatty acids that have applications in the cosmetics industry. Novel Approaches to Industrial intermediates (H.Mustafa, S.Johnson) In order to remain competitive, companies need to constantly review the processes used to produce chemical intermediates or final products. We are examining improved routes to amino-acids based on biotransformations and chemical transformations, and novel approaches to insect pheromones.

近期论文

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Exo- and endo-6-Chlorobicyclo[3.1.0]hexanes M S Baird and C B Reese Tetrahedron Letters, 1966, 1379-82. Thermal rearrangement of 9,9-dibromobicyclo[6.1.0]non-2-ene and related compounds M S Baird, D G Lindsay and C B Reese J Chem Soc, Chem Commun, 1968, 784-5. Thermal rearrangement of halogenocarbene adducts of cyclic olefins M S Baird, D G Lindsay and C B Reese J Chem Soc, Chem Commun, 1969, 1173-78. Action of heat on halogenocarbene adducts of cycloheptene and cis-cyclo-octene M S Baird and C B Reese J Chem Soc (C), 1969, 1803-7. Thermal rearrangements of 9,9-dibromobicyclo[6.1.0]non-4-ene and related compounds M S Baird and C B Reese J Chem Soc (C), 1969, 1808-13. Pyrolytic and electron impact studies on 1-bromp- and 1,1-dibromo-2,3-dimethylcyclopropanes M S Baird and C B Reese Tetrahedron Letters, 1969, 2117-20. Cyclopropanone reactions. Cyclobutanone derivatives from vinylic and acetylenic cyclopropanols H H Wasserman, R E Cochoy and M S Baird J Amer Chem Soc, 1969, 91, 2375-6. Cyclopropanones. IV. 1-Piperidinocyclopropanol and related systems H H Wasserman and M S Baird Tetrahedron Letters, 1970, 1729-30.