Biosynthesis of Natural Products
Code
10701
Academic unit
Faculdade de Ciências e Tecnologia
Department
Departamento de Química
Credits
6.0
Teacher in charge
Ana Maria Ferreira da Costa Lourenço, Ana Maria Félix Trindade Lobo
Weekly hours
4
Total hours
66
Teaching language
Português
Objectives
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.
Prerequisites
Credits in a general course of Organic Chemistry.
Subject matter
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.
7. Feromones and its practical importance.
8. Doping in sports.
Bibliography
1. A. M. Lobo & A. M. Lourenço (Ed.), “Biossíntese de Produtos Naturais", IST Press, Lisboa, 2007.
2. A. M. Lourenço,"Problemas em Biossintese de Produtos Naturais", Edinova, Lisboa, 1998.
3. P. M. Dewick “Medicinal Natural Products – A Biosynthetic Approach”, Wiley, Chichester, 2009.
Teaching method
Classes involve normal teaching that uses blackboard and power-point presentations. In tests and examinations, students are allowed to use their own notebooks, suggested bibliography for the discipline, or any other document sources, but not their computer or mobile phone. The work of this subject will end with a final presentation to the entire course of the web-molecule developped by the student on an individual basis. The file of the web-molecule should be up-loaded in the server made available until the last class of the course.
Evaluation method
A. Components of Evaluation and Assessment Elements
The UC has the Assessment Components 1. and 2. and their points refer Elements Evaluation of each component .
1. Experimental work ( 25%)
a) Preparation and performance on practical work ( 50 % ).
b ) Individual laboratory notebook ( 10 % ).
c ) Report and discussion ( 40 % ).
2 . Theoretical and problems ( 75 % ).
a) Delivery to the staff of all series of problems in due time.
b ) Molecule-web presentation and uploaded by the end of the semester .
c ) 2 tests the theoretical part ( 75 % ).
B. Approval in the UC:
1. Approval in the UC implies that in each of the Assessment Components , 1.Experimental and 2.Theoretical, the student has a classification ≥ 9.5 points.
2 . A rating of 1. a) , b ) and c) , together with the return of the problems series in due time, and presentation and up-load the molecule - web at the end of the semester, give the frequency of UC .
3 . The 2.Theoretical and problems rating is calculated as follows :
a) The arithmetic average of the two tests of the theory.
b )The delivery of all series of problems solved in due time throughout the semester .
c ) Selection and presentation of the molecule - web and on the dates indicated their up-load at the end of the semester .
4 . The score of A 2. c ) ≥ 9.5 ensures success in the course as well as access to written examinations for marks improvement, the latter being subject to payment of a fee if not done in the same academic year. The final mark is a result of the weights given in A 1. and A 2.