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.
Lectures, practical laboratory exercises, classroom exercises. Laboratory exercises are subject to the attendance of a safety lesson and a test. The articulation of the themes over time will follow the program with the exception of the theoretical part linked to the workshops which will be treated in advance of the practical exercises.
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 will be available on ARIEL platform.