Chemistry of Organic Natural Substances
A.Y. 2018/2019
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
Knowledge of the biosynthetic pathways leading to the major classes of natural products
Lesson period: First semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course cannot be attended as a single course. Please check our list of single courses to find the ones available for enrolment.
Course syllabus and organization
Single session
Responsible
Lesson period
First semester
Course syllabus
Goals
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.
Acquired skills
Knowledge of the biosynthetic pathways leading to the major classes of natural products.
Course content
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.
Suggested prerequisites
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).
Reference material
P. M. Dewick, Medicinal Natural Products. A Biosynthetic Approach, Third Ed., Wiley, Chichester, 2009
Assessment method
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.
Language of instruction
Italian
Attendance Policy:
Attendance is recommended
Mode of teaching:
Traditional
Website:
https://gsperanzacson.ariel.ctu.unimi.it/v5/home/Default.aspx
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.
Acquired skills
Knowledge of the biosynthetic pathways leading to the major classes of natural products.
Course content
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.
Suggested prerequisites
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).
Reference material
P. M. Dewick, Medicinal Natural Products. A Biosynthetic Approach, Third Ed., Wiley, Chichester, 2009
Assessment method
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.
Language of instruction
Italian
Attendance Policy:
Attendance is recommended
Mode of teaching:
Traditional
Website:
https://gsperanzacson.ariel.ctu.unimi.it/v5/home/Default.aspx
Professor(s)
Reception:
By appointment
Teacher's office - via C. Golgi 19 - 20133 Milano