LEARNING OUTCOMES

The course aims to provide an in-depth chemical culture through the study of the main functional groups and classes of reactions in organic chemistry. It also provides fundamental knowledge on the structure and metabolism of biomolecules, with particular attention to kinetic and thermodynamic aspects.

AIMS AND LEARNING OUTCOMES

The aim of the course is to provide an in-depth knowledge of the structure, reactivity and properties of complex molecules, starting with the classification and structure of the main functional groups in organic chemistry and the reaction pathways for the interconversion of these class of compounds. Students will learn the structure of the main synthetic macromolecules and natural macromolecules (lipids, proteins, carbohydrates, nucleotides) and their main anabolic and catabolic pathways, with particular attention to the role of enzymatic regulation and kinetic and thermodynamic considerations. Students should be able to correlate the signaling pathways activating different metabolic responses in different organs, with a focus on (dys)functional integration between different human organs.

PREREQUISITES

basic knowledge of Chemistry

TEACHING METHODS

Lectures and seminars

SYLLABUS/CONTENT

Functional groups, IUPAC nomenclature and classifications of main organic compounds. Single bonds: alkanes, alcohols, ethers, amines. Double bonds: alkenes, carbonyl compounds (aldehydes, ketones, carboxylic acids and functional derivatives of carboxylic acids), imines. Triple bonds: alkynes and nitriles. Saturated cyclic compounds: cycloalkanes. Aromatic hydrocarbons: benzene and main derivatives. Organic compounds of nitrogen, sulfur and phosphorus.

Properties. Stereochemistry.

Main organic reaction mechanisms: nucleophilic substitution, electrophilic addition, elimination, nucleophilic addition, nucleophilic acyl substitution, chemical reactivity of benzene.

Synthetic polymers:  polymerisation reactions and structure-property relations.

Molecules of biological interest: carbohydrates (monosaccharides, disaccharides, polysaccharides), amino acids and proteins, lipids, DNA and RNA. Coordination complexes.

Structure, properties and functions of aminoacids and proteins.

Enzymology. Enzymatic kinetics. Michaelis-Menten's equation. Enzyme inhibition. Allosteric enzymes. Properties and classification of enzymes. Vitamins as coenzymes.

Proteins that bind and transport oxygen; myoglobin and hemoglobin: structural properties and saturation curves. Cooperativeness.

Principles of bioenergetics and biosignalling.

Role of ATP and other phosphorous compounds. General principles of metabolism, catabolism, anabolism.

Carbohydrate metabolism: Glycolysis, gluconeogenesis and regulation. Ketone bodies. Glycogen synthesis, glycogen lysis and their reciprocal regulation in muscle and liver. Pentose phosphate pathway: oxidative and non-oxidative phase, metabolic meaning and regulation. Glutathione. Clinical tests for glucose metabolism.

The citric acid cycle. Pyruvate in mitochondria. Pyruvate dehydrogenase. AcetilCoA. Cycle regulation.

Oxidative phosphorylation. Flow of electrons on respiratory chain complexes. Structures and functions of cofactors involved in the transport of electrons. Proton gradient formation. Chemiosmotic coupling. ATP synthase. Structure and function. Coupling of ATP synthesis with the proton gradient and oxygen consumption.

Lipid metabolism. Lipases and regulation of the metabolism of triacylglycerol. Fatty acids: activation, transport mechanism, β-oxidation. Regulation. Energy yield for palmitate oxidation. Biosynthesis of fatty acids and triacylglycerol. Clinical tests for lipid metabolism.

Protein catabolism. Transamination and deamination of glutamate. Ketogenic and glucogenic amino acids. Urea cycle and its regulation. Clinical tests for protein metabolism.

Metabolic correlations between organs.

RECOMMENDED READING/BIBLIOGRAPHY

Lecture notes, aulaweb, chemistry books: J.McMurry, Fondamenti di Chimica Organica, Zanichelli; W.Brown, T.Poon, Introduzione alla Chimica Organica, EdiSES; J.G.Smith, Fondamenti di Chimica Organica, McGraw Hill; Lehninger Principles of Biochemistry, David L. Nelson, Michael M. Cox. Ed. Zanichelli.