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CHEMISTRY OF NATURAL SUBSTANCES

Academic year and teacher
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Versione italiana
Academic year
2020/2021
Teacher
CLAUDIO TRAPELLA
Credits
6
Didactic period
Primo Semestre
SSD
CHIM/06

Training objectives

The main objective of the course is to give students in-depth knowledge in terms of the chemistry of natural organic substances, with particular attention to their classification, structure, properties and biosynthesis.
The main knowledge gained will be:
-aminoacids: structure, properties and function
-proteins: structure, properties and function
-carbohydrates: structure, properties and function
-nucleic acids: structure, properties and function
-aminoacids: structure, properties and function
-terpens and alcaloids: structure, properties and function
-characterization and biosynthesis of natural organic compounds
Skills acquired during the teaching:
-recognition and classification of natural compounds
-prevision of physical and chemical properties of natural compounds based on chemical structure
-interpretation of reaction mechanism in main biosynthetic routes

Prerequisites

Basic Organic Chemistry knowledge is required.
Main topics:
-properties and reactivity of main organic compound classes
-stereochemistry
-relevant organic reactions and related mechanism

Course programme

The teaching is structured in 48 hours of frontal lessons.
Bioenergetic (4 h)
Biogenetic routes. Primary and secondary metabolites.
Aminoacids and sugars (6 h)
Properties and reactivity of aminoacids and sugars. Focus on stereochemistry.
Nucleic Acids (2 h)
Main organic reactions in biosynthesis:
Claisen, Aldol, Michael and Mannich, focus on reaction mechanism. (6 h)
Biosynthetic routes (30 h)
Acetate pathway, fatty acids, poliketides, prostaglandins, THC (6h)
Shikimate pathway, aromatic aminoacids synthesis and phenyl propanoids. (6 h)
Mevalonate pathway, terpens and steroids biosynthesis, steroids. (10 h)
Alcaloids: tropanic and pyrimidine alcaloids, nicotinic acid, cocaine, nicotine. (8h)

Didactic methods

Frontal lessons. All topics will be studied in details.

Learning assessment procedures

Final exam will consist in an oral talk. (30 minutes)
It will be structured in 4 questions:
1) amino acids and sugars: properties and reactivity
2) reaction mechanism of main organic reactions in biosynthetic routes
3)focus on a class of compounds and related metabolic pathway
4) terpens, alcaloids

Every questions will be evaluated with a maximum of 7 points, 2 more points will be gained depending on the chemical language used by the students.

Reference texts

Teacher’s handout.
Specific topics can be further developed in the following texts:

J. G. Smith - Fondamenti di Chimica Organica - McGraw Hill Education
P.M. Dewick - Chimica, Biosintesi e Bioattività delle Sostanze Naturali- Ed. Piccin