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Lecturer(s)
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Course content
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Lectures 1 and 2 Introduction to biosynthesis, primary metabolism and secondary metabolites, metabolism and structural diversity in the field of natural substances Lectures no. 3 and 4 Coenzymes and the Shikimic pathway. Introduction to secondary metabolites. Lectures 5 and 6 Biosynthesis and biomimetic synthesis of alkaloids Lectures 7 and 8 Biosynthesis and biomimetic synthesis of fatty acids and polyketids Lectures 9 and 10 Biosynthesis and biomimetic synthesis of isoprenoids Lectures 11 and 12 Biosynthesis and biomimetic synthesis of phenylpropanoids and their dimers and oligomers Lecture No. 13 "The Art of Total Synthesis" Application of Biomimetic Approach to Synthesis of Complex Natural Substances
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Learning activities and teaching methods
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Lecture, Dialogic Lecture (Discussion, Dialog, Brainstorming)
- Attendace
- 2 hours per semester
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Learning outcomes
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The aim of the lecture is to give to students a short overview of primary metabolism, enzymatic reactions, chemistry of cofactors in enzymatic reactions, and to show formation of major classes of secondary metabolites: shikimic derivatives, alkaloids, fatty acids, polyketones and isoprenoids. In many cases, the understanding of the individual reaction steps from the mechanistic point of view of organic chemistry has allowed to suggest better models describing metabolic pathways and enzymatic reactions. By the same way, isolation and structural determination of isolated secondary metabolites with interesting biological properties has led to the design of new reaction methods, catalysts or sequences that "mimic" various enzymatic reactions or metabolic pathways. Biomimetic approach in the synthesis of complex organic compounds thus mimics the enzymatic and non-enzymatic transformations used in the biosynthesis of metabolites and their derivatives. The aim is to show to students that our understanding of the reaction mechanisms of many of these biotransformations has allowed us to design new catalysts / reagents that have allowed us to prepare both natural products, their synthetic derivatives and substances only remotely structurally similar to natural substances.
Acquired competencies - Recognize and order natural substances according to their main classes - Recognize the biological and chemical origin of these substances - Propose the likely mechanism of formation for many of these substances - Understand the pitfalls originated from the biomimetic approach in the synthesis of natural substances
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Prerequisites
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Knowledge of basic organic, inorganic and physical chemistry.
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Assessment methods and criteria
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Mark, Oral exam, Seminar Work
Pre-exam will be granted for a seminar work (see below). Seminar work must be given at least 7 days before the oral exam. Seminar work (maximum 5 pages A4, Times New Roman 11, line 1.1, including pictures, schemes and list of used literature) will be based on analysis of natural product synthesis (molecule taken from literature - molecules selected by lecturer) with a focus on mechanism and selectivity of key reaction steps. During the oral exam, this work will serve as the basis of the exam. Questions will depend on the seminar work, but will not be LIMITED to. A detailed discussion of individual synthetic transformations will then be the basis for student assessment.
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Recommended literature
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A. E. Osbourn, V. Lanzotti ed. (2009). Plant-derived natural products : synthesis, function, and application. Dordrecht, Springer.
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L. Macholán. (2013). Sekundární metabolity. Masarykova univerzita v Brně.
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Rajesh Arora ed. (2010). Medicinal plant biotechnology. Cambridge, CABI.
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Z. Vodrážka. (1996). Biochemie. Academia Praha, Praha.
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