TOPIC n.1 (1 CFU) Main reaction mechanisms involved in hte synthesis of secondary metabolites: alkylation, transposition, condensation, redox reactions, oxidative coupling in phenols, glycosylation reactions. Carbohydrates. Definition and classification.Monosaccharides. Aldoses e chetoses, configuration, D and L series. Emiacetalic cyclic structures, Fischer projections, Haworth formulae, conformation of pyranosides. Mutarotation. Main monosaccharides: glucose, fructose, ribose. Reactions of monosaccharides: formation of esters and ethers, oxydation e riduction, reactions with amines. Formation of O- and N- glycosides. Examples of pharmacologically relevant glucosides. Hydrolysis of glucosides. Vitamine C, aminosugars.
Disaccharides. Structure and property of the main disaccharides: maltose, cellobiose, lactose, saccharose. Sweeteners. Structrure and function of the main polisaccharides: starch, cellulose, glycogen, gums, cyclodextrins.
TOPIC n.2 (1 CFU) The biogenetic pathways of acetate: fatty acids and polyketides. Lipids. Definition and classification. Fatty acids and triacylglicerols. Preparation of natural soaps. Micelle formation. Synthetic detergents. Phospholipids: structure and biological importance. Prostaglandins and steroids. Poliketides: biological activity. Examples of biosynthesis: emodin, hypericin, usnic acid, griseofulvin. Sinthessi of aromatic poliketides, simple phenols, antraquinones. Tetracyclines. Macrolide antibiotics.
TOPIC n.3 (1 CFU) The mevalonate and methylerytritol-phosphate biogenetic pathways: terpenoids and sterols. Terpenes: classification and biosynthesis, chemical properties. Steroids: structure and stereochemistry of plant and animal sterols, steroidal saponins, phytosterols. Examemples of biosynthesis: tujone, pinene, menthol, thymol. The biogenetic pathway of shikimic acid. Biosynthesis of phenols, poliphenols and phenylpropanoids. Cinnamic acids and their transfomraiton products (estragol, eugenol, anetol, etc). Reactions of oxidative coupling: lignans, neolignans e lignin. Benzoic acids, coumarins and their derivatives. Furanocoumarines: photodynamic activity, biosynthesis of psoralene. Flavonoids and isoflavones. Terpenoid quinones . Natural colorants and elements of tinctorial chemistry.
TOPIC n.4 (1 CFU) Aminoacids. Structure and configuration. Behaviour of aminoacids in solution: acidity and basicity. Isolectric point. Nucleci acids: Composition, structure of nucleosides and nucleotides. Structure nucleic acids. Three dimensional structureof the double helix.
Alkaloids. Biological amines and their activity. Pyrrolidin and tropa alkaloids: hyosciamin, cocaine, atropine. Alkaloids isoquinolinic: reticuline, papaverine, morfine, codeine and berberine. Pyridine alkaloids: biosynthesis of nicotinic acid, nicotine and anabasine. Indole alkaloids: psylocibine, lysergic acid.
TOPIC n.5 (1 CFU ): Laboratory tutorials, dealing with the main extraction, isolation and identification of natural organic substances.
P.M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali- Piccini (Ed. Italiana).
Organic Chemistry text book at university level, for instance:
W. H. Brown: Introduzione alla Chimica Organica, EdiSES (with exercise text book) J. Mc Murry: Fondamenti di Chimica Organica, ed., Zanichelli
Slides, laboratory tutorial guidelines and other teaching materials will be given by the teacher during the course and made available on the on-line teaching site, from which they can be downloaded in pdf format.