Chemistry of organic natural substances

A.Y. 2021/2022
Overall hours
Learning objectives
The course aims at giving a general overview of the chemistry of natural products with emphasis on secondary metabolites, their occurrence, structure, biosynthesis and properties.
Expected learning outcomes
Students will acquire knowledge of the biosynthetic pathways leading to the major classes of natural products, being able to appreciate their relevance in various application fields.
Course syllabus and organization

Single session

More specific information on the delivery modes of training activities for academic year 2021/22 will be provided over the coming months, based on the evolution of the public health situation.
Course syllabus
Primary and secondary metabolism. Enzymes and coenzymes. Mechanistic and stereochemical aspects of enzyme-catalyzed reactions. Oxidation, reduction, carboxylation, decarboxylation, alkylation and glycosylation reactions. Biosynthetic pathways. Methods of studying secondary metabolism. Use of isotopically labelled compounds (tracer technique).
Terpenes - Structural isoprene rule. Biosynthesis of IPP and DMAPP. Monoterpenes. Sesquiterpenes. Diterpenes. Triterpenes. Carotenoids.
Steroids - Conversion of lanosterol into cholesterol. Phytosterols. Cardioactive glycosides. Steroidal saponins. Vitamin D. Corticosteroids. Progestogens. Androgens. Oestrogens.
The shikimate pahtway - Aromatic amino acids. Phenylalanine derivatives via cinnamic acid. Phenylpropanoids. Lignans and lignins. Flavonoids. Isoflavonoids.
The acetate pathway - Aromatic polyketides. Naphthoquinones and anthraquinones. Antibiotics. Fatty acids.
Prerequisites for admission
Knowledge of basic principles in organic chemistry (functional groups, reactivity, reaction mechanisms). Basic knowledge of the main classes of naturally occurring organic compounds (aminoacids, peptides, carbohydrates).
Teaching methods
Teaching Resources
P. M. Dewick, Medicinal Natural Products. A Biosynthetic Approach, Third Ed., Wiley, Chichester, 2009
Assessment methods and Criteria
Oral examination in an scheduled exam session with one/two open-ended questions. Evaluation criteria: knowledge and mastery of course content; ability to understand the multidisciplinary aspects of the course; articulation and use of appropriate terminology.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Lessons: 48 hours
Professor: Speranza Giovanna