Chemistry of Natural Products
A.Y. 2024/2025
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.
Lesson period: First semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Responsible
Lesson period
First semester
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.
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 mode: classroom lessons supported by projected material with discussion.
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
Shifts:
Turno
Professor:
Speranza GiovannaEducational website(s)
Professor(s)
Reception:
By appointment
Teacher's office - via C. Golgi 19 - 20133 Milano