Biosynthesis of Natural Products
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.
Ana Maria Ferreira da Costa Lourenço
Weekly - 4
Total - 56
Basics of organic chemistry: chemical reaction mechanisms and structural analysis.
1. A. M. Lobo & A. M. Lourenço (Ed.), “Biossíntese de Produtos Naturais", IST Press, Lisboa, 2007.
2. J. Mann "Secondary metabolism", Claredon press, Oxford, 1987.
3. P. M. Dewick “Medicinal Natural Products – A Biosynthetic Approach”, Wiley, Chichester, 2009.
4. A. M. Lourenço,"Problemas em Biossintese de Produtos Naturais", Edinova, Lisboa, 1998.
Theoretical classes are presented on power-point that are followed by more detailed explanations on the board. The tests and exams are carried out online and with consultation of the notes of the classes, bibliography recommended for the discipline, or any other bibliographic sources selected by the students.
There will be three practical classes for the preparation of a metabolite belonging to a specific biosynthetic group. The work is in group of two students.
A. Assessment Components and Evaluation Elements
The UC has the Assessment Components 1 and 2 and its paragraphs refer the evaluation elements for each component.
1. Experimental work (20%)
a) Preparation and performance in carrying out practical work (60%).
b) Report and discussion (40%).
2. Theoretical (80%)
Two written tests of the theoretical part or exame (80%).
B. Approval to UC
1. Approval UC implies that in each of the evaluation components, 1. Experimental work and 2. Theoretical, the student has a classification ≥ 9.5 points.
2. The classification 1. Experimental gives the frequency of UC.
3. The theoretical classification is calculated as the arithmetic average of the two tests or the classification of the Recurso exam. The Recurso exam can also be used to improve the theoretical classification.
4. Students who have frequency from previous years will just have to make the theoretical part. The previous classification is used in the calculation weighted towards the final grade as described above.
1. Use of natural products. Drugs of natural origin. Present impact.
2. Primary and secondary metabolism. Enzymatic reactions of the secondary metabolism and their analogy with organic reactions. Classification of natural products according to their biosynthetic origin. Biosynthetic methods.
3. Derivatives from the acetate unit. Beta-ketonic chains. Fatty acids, oils, fats and polyketides. Acetylenes. Prostaglandins and analogues. Cyclization of polyketonic chains. Aromatic polyacetates. Tetracyclines.
4. The isoprenic unit. Isoprenoids. Monoterpenes, diterpenes and triterpenes. Steroids. Tetraterpenes. Carotenoids.
5. Shikimic acid derivatives. Aromatic aminoacids. Cinnamic acids, phenylpropenes. Lignans and lignins. Coumarins. Flavonoids and stilbenes.
6. Alkaloids derived from ornithine, lysine, phenyl-alanine, tyrosine, tryptophan and antranylic acid. Alkaloids derived from purine: caffeine. Steroidal alkaloids.