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Wersja polska

Course code: NBSS20075o10
Semester: 2010/2011 winter
Name: Biosynthesis and Synthesis of Chiral Biologically Active Compounds
Major: Biotechnology
Study Type: second cycle
Course type: compulsory
Study Semester: 2
ECTS points: 6
Hours (Lectures / Tutorials / Other): 45 / 0 / 0
Lecturer: prof. dr hab. Czesław Wawrzeńczyk
Language of instruction: Polish


Learning outcomes: Students can predict the most important spectral properties of chemical substances. Students can predict the correct or most probable structure from experimental data. After completing the course student has insight in the biosynthetic pathways of isoprenoids. He is familiar with their biological properties and understands the connections between the structures of isoprenoids and their biological activities. After the course students know various aspects of activity of chiral molecules, including their synthesis and practical applications. They are also familiar with important methods of obtaining pure enantiomers in particular types of the reactions. They know various aspects of activity of chiral molecules, including their synthesis and practical applications. They are also familiar with important methods of obtaining pure enantiomers in particular types of the reactions.

Competences: Students are able to isolate the organic compounds, select the most appropriate solution for a given analytical problem and evaluate the results of the analysis. Completing the course makes possible to project the synthesis of isoprenoid compounds with particular biological properties. The students understand the detailed nomenclature of chiral compounds and the applications of chiral auxiliaries and chiral catalysts in modern stereochemistry.

Prerequisites: Organic Chemistry, Biochemistry

Course content: The 1H, 13C, 31P, 19F nuclear magnetic spectroscopy and application of NMR methods for structure determination of organic compounds. Two dimensional spectroscopy 1H-1H and 1H-13C NMR. The application of combined IR, UV and NMR methods for the organic compounds identification. Biosynthesis of isoprenoids: monoterpenes, sesquiterpenes, diterpenes and steroids. Occurring of these groups of compounds in the plants and animal world. The biological activity of isoprenoids, especially natural and synthetic isoprenoid lactones. Chemical synthesis of some isoprenoids with useful biological activities. General principles of asymmetric synthesis. Application of chiral auxiliaries and chiral catalysts. Enantioselective reduction and oxidation. Hydrolysis and esterification.

Recommended literature: 1. Spectroscopic identification of organic compounds, R.M. Silverstein and G.C. Bassler, John Wiley and Sons, Inc. 1997 2. Metody spektroskopowe i ich zastosowanie do identyfikacji związków organicznych, Praca zbiorowa pod redakcją W. Zielińskiego i A. Rajcy, Wydawnictwo Naukowo-Techniczne Warszawa 1995 3. Natural Product Reports, 1993-2005 4. Diterpenes of Flowering Plants, F. Seaman, F. Bohlmann, C. Zdero, T.J. Mabry, Springer-Verlag 1990 5. Najcenniejsze olejki eteryczne, Józef Góra, Anna Lis, Wydawnictwo Uniwersytetu UMK, Toruń 2005 6. David J. Ager Handbook of chiral chemicals, Marcel Dekker, INC, New York, 1999 7. Garry Procter, Asymmetric synthesis, Oxford University Press, 1996 8. Cyntha A. Challener, Chiral intermediates, Ashgate Publishing Company 2001.

Assessment methods: Written and oral exam, the minimal level of knowledge required to pass the course is 60%.

Comment: Course consits of three topics: TB 067.1. Structure determination of bioactive compounds II (dr inż. Mirosław Anioł), TB 067.2. Isoprenoids: biosynthesis, occurring and biological activity (prof. dr hab. Czesław Wawrzeńczyk), TB 067.3. Asymmetric synthesis (dr Teresa Olejniczak).