Carbohydrates. Structural types, stereochemistry and nomenclature of monosaccharides. Sources and function. Chemistry of monosaccharides. Reactions of the hydroxyl group. Reactions at the anomeric centre. Glycosides. Formation and hydrolyses. Methods for determine the size of sugar rings. Oligosaccharides and polysaccharides. Determination of the structure and syntheses of polysaccharides. Structural characteristics and biological properties (glycogen, starch, cellulose, hitine). Nucleosides, nucleotides and polinucleotides: structure, reactivity and synthesis. Amino acids and proteins. Properties and stereochemistry of amino acids. Reactions of amino acids in vitro and in vivo. Syntheses of amino acids. Resolution of the amino acid racemates. Enantioselective syntheses of amino acids. Peptides and proteins. Syntheses of peptides and proteins. N-protecting groups. Activation and reaction: solid faze syntheses. Some linear and cyclic peptides and proteins. Terpenoids. General routes of biogenesis. Structure determination. Monoterpenoids. Sesquiterpenoids. Diterpenoids. Triterpenoids. Tetraterpenoids. Polyterpenoids. Steroids. Cholesterol. Bile acids. Sex hormones. Saponins. Vitamin D. Phytosterols. Stereochemistry, biogenesis, chemical syntheses and transformations. Phenolics. Structural types. Natural occurrence. Isolation and structure elucidation. Biogenesis via acetate pathway. Laboratory syntheses. Shikimic acid. Aromatic amino acids and phenylpropanoids. Biogenesis via shikimate pathway. Cinnamic acids, flavonoids and anthocyanidins. Alkaloids. Structural characteristics. Natural occurrence. Isolation and structure elucidation. Biosynthesis of alkaloids. Alkaloids derived from ornithine and lysine. Alkaloids derived from phenylalanine and tyrosine. Alkaloids derived from tryptophan. Synthesis of alkaloids.
- to be able to described structures of natural organic products and explain their physical and chemical properties;
- to compare the structure of natural organic products and their chemical reactivity;
- to interpret important biochemical processes of biologically active secondary metabolites;
- to implement fundamental knowledge of organic chemistry in planning of synthesis of natural organic products;
- to have a working knowledge of a broad set of modern synthetic methods related to the total synthesis of bioactive natural products;
- to explain main reaction mechanisms in synthesis and biosynthesis of compounds, especially stereoselective reactions;
- to present adequate skills in technical writing and oral presentations.
- J. Clayden, N. Greeves, S.Warren, P. Wothers, Organic Chemistry, 2 izdanje, Oxford University Press, 2012.
P. M. Dewick, Medicinal Natural Products. A Biosynthetic Approach. 3. izdanje, Chichester, John Wiley & Sons, 2009.
K. C. Nicolaou, E. J.Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods. Wiley 1996.
4. K. C. Nicolaou, , S. A. Snyder, Classics in Total Synthesis II: More Targets, Strategies, Methods. Wiley 2003.
- S. H. Pine, Organska kemija, Školska knjiga 1994.
J. Mann, R.S. Davidson, J.B. Hobbs, D.V. Banthorpe and J.B. Harborne, Natural Products, Their Chemistry and Biological Significance, Longman, 1996.