Biosynthesis of Natural Products
Faculdade de Ciências e Tecnologia
Departamento de Química
Teacher in charge
Ana Maria Félix Trindade Lobo
The objectives of the discipline include the presentation of the major biosynthetic study methods, as well as the most important metabolic pathways used by the cell in the production of metabolites, specially secondary metabolites. Such knowledge will provide the student with the capacity to rationalize the formation of natural products, the prediction of the structure of novel compounds and their expected metabolism.
Students should have a least an introductory knowledge of organic chemistry, which should include the recognition of the major functional groups and the knowledge of the most common reaction mechanisms.
T HEORETICAL CLASSES
1. Medicinal plants and natural products – a brief introduction
Overview on the use of natural products. Chemical products from terrestrial and marine origin. Present impact and recent developments.
2. Primary and secondary metabolism
Primary and secondary metabolism. Enzymes involved in the biosynthesis of natural products. Enzymatic reactions of the secondary metabolism and their analogy with organic reactions. Classification of natural products according to their biosynthetic origin.
3. Natural products derived from acetate.
Formation of beta-ketonic chains. Fatty acids, oils, fats and polyketides. Acetylenes. Prostaglandins and analogues. Cyclization of polyketonic chains. Aromatic polyacetates. Tetracyclines. Methos of elucidation of biosynthetic pathawys.
4. Natural products derived from mevalonate and deoxyxylolose phosphate.
Formation of the isoprenic unit. Isoprenoids. Biosynthesis of regular and irregular monoterpenes. Iridoids. Sesquiterpenes, diterpenes, and sesterterpenes. The squalene molecule, and squalene epoxide. Triterpenes, steroids, and tetraterpenes. Carotenoids.
5. Natural Products derived from shikimic acid
Aromatic aminoacids. Cinnamic acids, phenylpropenes. Lignans and lignins. Coumarins. Flavonoids. metabolites. and benzoic acids. Phenolic compounds. Coumarins. Mixed biosynthesis: natural products derived from acetate and mevalonate units.
Alkaloids derived from ornithine, lysine, phenyl-alanine, tyrosine, tryptophan and antranylic acid. Alkaloids derived from purine: caffeine. Mixed biosynthesis: alkaloids derived from tryptofan and mevalonate (ex. LSD); steroidal alkaloids.
1. A. M. Lobo & A. M. Lourenço (Ed.), “Biossíntese de Produtos Naturais", IST Press, Lisboa, 2007.
2. A. M. Lourenço,"Problemas em Biossíntese de Produtos Naturais", Edinova, Lisboa, 1998.
3. P. M. Dewick “Medicinal Natural Products – A Biosynthetic Approach”, Wiley, Chichester, 2009.
Classes involve normal teaching that uses blackboard, and power-point presentaions. In tests and examination, students are allowed to use their own notebooks, suggested bibliography for the discipline, or any other document sources.
- Two option tests.
- Final exam for those who: a) didn''''''''''''''''''''''''''''''''t attend the tests; b) have a negative mean classification in the tests; c) wish to improve their final classification.