By the end of the course, students should be familiar with the main natural substances produced by the secondary metabolic pathways covered in class. A continuous comparison between "classical" chemistry and metabolic pathways helps define the biosynthetic pathways covered.
Course Prerequisites
Si consiglia di avere una padronanza almeno discreta degli argomenti trattati nei corsi di Chimica Organica di base. Attraverso i meccanismi di reazione coinvolti nei processi indagati si impara a riconoscere una sostanza naturale.
Teaching Methods
Classroom lectures are conducted using slides and scientific articles. Continuous interaction with the student during the lectures helps consolidate the basic chemistry concepts underlying secondary metabolism.
Assessment Methods
Oral examination with a presentation focused on a secondary metabolite.
Texts
[1] P. M. Dewick, “Medicinal Natural Products: A Biosynthetic Approach 3rd Edition”, Wiley, 2009. [2] T. Hudlicky and J. W. Reed, “The Way of Synthesis”, Wiley-VCH, 2007. [3] Kurt Faber. “Biotransformations in Organic Chemistry.”, Ed. Springer.
Contents
The course is structured as follows: After an introduction to organic chemistry reactions that occur in vivo in biological systems and the concepts of biosynthetic building blocks, we move on to a detailed description of the four main groups of natural substances, divided based on their biosynthesis. 1) The Acetate Pathway: prostaglandins, macrolides, etc.; 2) The Shikimate Pathway: typical of the plant world and a precursor to many important substances; 3) The Terpene Pathway: mevalonic and non-mevalonic, how monomers are produced, and how to learn about cationic domino reactions underlying the biosynthesis of complex terpenes (such as Taxol) and steroids (e.g., cholesterol). 4) Alkaloids: a class of substances composed of different biosynthetic pathways that share some structural features. Finally, the applications of these basic reactions for the synthesis of natural substances will be covered in class. The concept of disconnection and synthetic equivalent will be reviewed, and a review will be provided from the first syntheses that appeared in the literature up to the most innovative protocols for first constructing and then decorating the target compound.
Course Language
Italian
More information
Interdisciplinary seminars will be held as part of the course.
