C7640 - CHIMICA E PROPEDEUTICA BIOCHIMICA

Learning outcomes

The Course of Chemistry and Introductory Biochemistry aims at providing the bases for the comprehension of the primary laws governing matter and its transformations, with particular attention to biological phenomena at atomic and molecular levels, in relation to biomedical applications. The Course of Chemistry and Introductory Biochemistry is divided in 8 teaching units: • -Teaching Unit 1. The structure of the atom, the periodic table of elements and chemical bonds (CFU =0.5). • -Teaching Unit 2. States of matter and principles of thermodynamics (CFU =0.5). • -Teaching Unit 3. Mixtures and solutions and the colligative properties of solutions (CFU=1). • -Teaching Unit 4. General information on chemical reactions, kinetics and chemical equilibrium (CFU=0.5). • -Teaching Unit 5. Acids, bases, salts, pH, buffer solutions; redox reactions and electrochemistry (CFU= 1). • -Teaching Unit 6. Properties of carbon and reactivity of organic compounds, hydrocarbons, alkyl halides, aromatic hydrocarbons and derivatives (CFU= 0.5). • -Teaching Unit 7. Functional groups and isomers: alcohols, phenols, ethers, thiols and thioethers; aldehydes and ketones; carboxylic acids and derivatives, amines and amides (CFU= 1). • -Teaching Unit 8. Amino acids and proteins, carbohydrates, lipids, nucleotides and polynucleotides (CFU= 1). The specific learning outcomes of the Course will be set out in Web Guides according to DM n. 418/2025.

Course contents

According to Decreto Ministeriale n. 418 del 30-05-2025.

Teaching Unit 1. The structure of the atom, the periodic table of elements and chemical bonds (CFU =0.5).

To describe and to interpret:

- The composition of matter. Foundations of the atomic theory. Structure of the atomic nucleus, neutrons, and protons. Atomic number and mass number. Atomic mass. Isotopes.

- Overview of the magnetic properties of the nucleus as a basis for the diagnostic tool of nuclear magnetic resonance.

- Elements and compounds: mole and molecule. Quantum numbers, orbitals, the Pauli exclusion principle and the Heisenberg uncertainty principle. Hund's rule. The electronic configuration of elements.

- Radioisotopes and radioactivity. Radioactive decay (α, β, positron and gamma radiations, X-rays): units of measurement also in relation to biological toxicity, correlations of interest for biomedical applications.

- The periodic table of elements. Periodic properties: external electronic configuration, atomic volume, ionization potential, electron affinity, electronegativity. Chemical elements of biological relevance. The octet rule.

- Molecules and polyatomic ions. Molecular mass.

- The chemical bond. Bonding orbital. Covalent bond: homopolar, heteropolar, dative. Bond with delocalized electrons. The ionic bond. Hybridization of orbitals: sp, sp2, sp3. VSEPR theory. Sigma and pi molecular orbitals. Bond angles.

- Nomenclature and structure of the main inorganic compounds of biomedical interest. Examples of the structures of binary and ternary chemical compounds, writing and identifying structural formulas (oxides, acids, bases, salts). IUPAC and traditional nomenclature. Weak interactions (hydrogen bonding and van der Waals forces) and hydrophobic interactions.

Teaching Unit 2. States of matter and principles of thermodynamics (CFU =0.5).

To describe and to interpret:

- The solid state: ionic, molecular, covalent, and metallic solids.

- The gaseous state. Absolute temperature. Boyle's, Charles', and Gay-Lussac's laws. Equation of state for ideal gases. Real gases and the Van der Waals equation. Avogadro's law. The concept of the mole and Avogadro's number. Overview on the kinetic theory of gases. The Maxwell-Boltzmann law.

- Gases and vapors. Gas-liquid equilibrium: vapor pressure.

- The liquid state: boiling, heat of evaporation. Phase diagrams: comparison between water and carbon dioxide. Surface tension. Relevance of changes of state in medicine: evaporation of sweat and thermoregulation. Application of the gas law to respiration.

- Thermodynamic systems. The principles of thermodynamics. Definitions of state functions. Enthalpy. Exothermic and endothermic transformations (changes of state). Entropy. Gibbs free energy. Reversible and irreversible transformations (exergonic, endergonic transformations). Free energy and chemical equilibrium.

Teaching Unit 3. Mixtures and solutions and the colligative properties of solutions (CFU=1).

To describe and to interpret:

- Types of mixtures: homogeneous and heterogeneous (dispersions, suspensions, colloids, aerosols).

- Types of solutions: gaseous, liquid and solid solutions.

- Solubility: water as a solvent. Water and ionic solutes, properties of electrolytes. Electrolytes in biological fluids. Water and molecular solutes. Solubility of gases in liquids: Henry's law.

- Units of measurement for solution concentration: weight/weight, weight/volume, and volume/volume percent concentrations. Molarity, mole fraction. The concept of equivalent in biomedical applications

- Concentration in gas mixtures: Dalton's law. Air and its composition, inspired air and exhaled air. Examples of solutions relevant to biomedical aspects.

- Definition of colligative property. Solvent-solute interactions. Raoult's law. Vapor pressure lowering. Elevation of boiling point. Depression of freezing point.

- Electrolytic solutions and the van't Hoff factor. Types of membranes and transport: diffusion, osmosis, and osmolarity. Comparison of the osmotic properties of solutions.

- The osmolarity of intracellular and extracellular fluids. Isotonic, hypertonic, and hypotonic solutions.

Teaching Unit 4. General information on chemical reactions, kinetics and chemical equilibrium (CFU=0.5).

To describe and to interpret:

- Definitions of chemical reactions.

- Conservation of mass, energy, and electric charge. Reversibility. Types of chemical reactions. Neutralization reactions. Precipitation reactions. Redox reactions. Balancing reactions. - Definition of reaction kinetics. Multistep reactions. Factors that influence the reaction rate. Reaction order and molecularity. Arrhenius' law and the theory of effective collisions. Activation energy. Transition state theory. Catalysts: homogeneous and heterogeneous catalysts.

- Notes on biological catalysts: enzymes.

- Chemical equilibrium.

- Reversible and irreversible reactions. Equilibrium constant and law of mass action. Homogeneous and heterogeneous chemical equilibrium. Difference between chemical equilibrium and steady state. Principle of moving equilibrium. The reaction quotient. Effect of temperature on the equilibrium constant. Multiple equilibria. Heterogeneous solid-liquid equilibria. Solubility product, common ion effect. Relevance of chemical equilibria in biological processes.

Teaching Unit 5. Acids, bases, salts, pH, buffer solutions; redox reactions and electrochemistry (CFU= 1).

To describe and to interpret:

- Arrhenius theory. Bronsted and Lowry theory. Overview on Lewis theory. The autoprotolysis reaction of water. Kw. The concept of pH and pOH. Dissociation constants, Ka and Kb. Strong and weak acids, pKa and pKb. pH indicators. The pH of a strong acid/base or weak acid/base solution. Polyprotic acids and polyprotic bases. Relative strength of an acid and a base. Acid-base reactions. Relationship between chemical structure and acid strength. Salts, acidic or basic behavior of salts in water, hydrolysis constant. Solubility and pH, examples of biomedical interest: calcium oxalate and calcium phosphate. The topics will be covered with numerical examples to aid understanding of the phenomena described.

- Buffer solutions, examples of weak acid and weak base buffers. The Henderson-Hasselbalch equation. Efficiency of a buffer system. Acid-base balance in biological fluids: the carbonic acid/bicarbonate buffer, the dihydrogen phosphate/hydrogen phosphate buffer, proteins as buffer systems. Blood pH and blood buffers. The importance and function of buffers in biomedical field.

- Oxidation number and redox reactions. Electrochemical systems. Definition of anode and cathode. Types of conductors.

- Half-cells. Standard redox potentials. The Nernst equation. Spontaneous reactions and chemical work: relationship between Gibbs free energy change and potential difference. The relationship between reduction potentials and the equilibrium constant. Concentration cells.

- Importance of redox reactions in biomedical field.

Teaching Unit 6. Properties of carbon and reactivity of organic compounds, hydrocarbons, alkyl halides, aromatic hydrocarbons and derivatives (CFU= 0.5).

To describe and to interpret:

- Properties and hybridization of carbon. Functional groups. Representation of carbon compounds.

- General rules of IUPAC nomenclature.

- Oxidation and reduction in organic chemistry. Types of organic reactions. Inductive effect: electron donating, electron withdrawing. Delocalization effect or mesomer.

- Bond breaking: homolytic and heterolytic. Carbocations and carboanions. Stability of carbocations. Nucleophiles and electrophiles.

- Acidity and basicity of organic compounds.

- Saturated and unsaturated hydrocarbons.

- Alkanes and cycloalkanes: IUPAC nomenclature, chemical and physical properties, and characteristic reactions. Bond strain in cycloalkanes. Reactions of alkanes: oxidation, radical substitution.

- Alkenes: IUPAC nomenclature, chemical and physical properties, and main reactions (electrophilic addition, stability of carbocations). Electron delocalization and conjugated dienes.

- Cyclic and heterocyclic hydrocarbons. Halogen derivatives of hydrocarbons. Reactions of alkyl halides: nucleophilic substitution with SN2 and SN1 mechanisms, elimination reactions with E1 and E2 mechanisms.

- Benzene, aromatic compounds, and Huckel's rule.

- Nomenclature of aromatic hydrocarbons. Benzene derivatives. Reactions of benzene: electrophilic aromatic substitution. Activating and deactivating effect of substituents.

- Toxicity of aromatic compounds.

Teaching Unit 7. Functional groups and isomers: alcohols, phenols, ethers, thiols and thioethers; aldehydes and ketones; carboxylic acids and derivatives, amines and amides (CFU= 1).

To describe and to interpret:

- Chemical-physical properties and nomenclature. Reactions of alcohols: dehydration, oxidation, nucleophilic substitution. Alcohols of biomedical relevance: ethanol. Aromatic alcohols, phenol and derivatives; acidity of phenol. Ethers. Thiols and thioethers. Epoxides.

- Chemical-physical properties and nomenclature of aldehydes and ketones. Reactions of aldehydes and ketones: oxidation, reduction, nucleophilic addition reactions. Hemiacetals and hemiketals, acetals and ketals. - Properties of hydrogen alpha to the carbonyl. Keto-enol tautomerism and its biological importance.

- Aldol condensation reaction. Quinones and hydroquinones. An example of biomedical relevance: ubiquinone.

- Chemical-physical properties and nomenclature. Reactions of carboxylic acids: salification, nucleophilic acyl substitution.

- Carboxylic acid derivatives: acyl halides, anhydrides, esters and thioesters, amides, acyl phosphates. Fisher esterification. Basic and acid hydrolysis of esters. Claisen condensation. Reactions of carboxylic acids containing other functional groups: formation of lactones and decarboxylation of ketoacids.

- Organic derivatives of phosphoric acid. The importance of acyl phosphates in biochemistry. - Chemical-physical properties and nomenclature of amines. Basicity and reactions of amines: nucleophilicity of amines, alkylation. Nitrosamines. Quaternary ammonium: choline. Imines or Shiff bases.

- Examples of biomedical importance: urea.

- Hydrolysis reactions of amides.

- Definition and types of isomerism: constitutional isomers and stereoisomers (conformational and configurational isomers). - Specific optical rotatory power. Fischer convention and dextrorotatory/left-handed convention. - Diasteromers, epimers, anomers, and meso compounds. Racemic mixtures. Notes on priority rules. E/Z convention and R/S convention. - Significance of enantiomers, diastereoisomers, and mesoforms in biomedical sciences.

Teaching Unit 8. Amino acids and proteins, carbohydrates, lipids, nucleotides and polynucleotides (CFU= 1).

To describe and to interpret:

- Structure and nomenclature of amino acids, abbreviated names. Classification of amino acids by R group. Essential or nonessential amino acids.

- Identification and characteristics of the side chains of protein amino acids. Stereochemistry of amino acids and representation according to the Fischer convention.

- Acid-base properties of amino acids and isoelectric point.

- The peptide bond and its formation. Characteristics of the peptide bond. Structural levels of proteins: primary, secondary, tertiary, and quaternary structure. Weak interactions and disulfide bonds.

- Structure, nomenclature, and stereochemistry of carbohydrates. Monosaccharides: isomers, epimers, anomers, and tautomers. Aminosugars. Cyclization of monosaccharides. Mutarotation. Reactions of monosaccharides: oxidation, reduction, Maillard reaction and Amadori products, condensation. The glycosidic bond. Disaccharides. Oligosaccharides and their derivatives. Polysaccharides: homopolysaccharides (starch, cellulose, glycogen) and heteropolysaccharides (glycosaminoglycans).

- Structure and nomenclature of fatty acids. Saturated and unsaturated fatty acids. Essential fatty acids. Unsaturation and physical and chemical properties. Triglycerides and their functions: oils and fats. Complex lipids: glycerophospholipids, sphingolipids, glycolipids. Cholesterol and steroid derivatives of biomedical interest.

- Nitrogenous bases: definition and structural characteristics of nucleosides and nucleotides. Nucleotides and polynucleotides. Chemical structure and biological importance of ATP and other free nucleotides. Phosphodiester bond.

Readings/Bibliography

- FA Bettelheim et al; Chimica e Propedeutica biochimica, Edises.

- T Bellini; Chimica Medica e Propedeutica Biochimica, Zanichelli.

- L Binaglia & B Giardina; Chimica e Propedeutica Biochimica, McGrawHill.

- KJ Denniston et al; Chimica Generale, Chimica Organica, Propedeutica Biochimica, McGrawHill

- S. Marini et al; Chimica e Propedeutica Biochimica, Piccin.

Teaching methods

The lectures will be held in the manner specified in the Dedicated web site.

Assessment methods

According to Decreto Ministeriale n. 418 del 30-05-2025 (allegato 2).

The exam for each course will be a written exam (lasting 45 minutes) with 31 questions divided into:

• 15 multiple-choice questions with 5 answer options, only one of which is correct;

• 16 fill-in-the-blank questions.

The exam score is awarded as follows:

• 1 point for each correct answer

• 0 points for each omitted answer

• minus 0.25 (- 0.25) points for each incorrect answer.

A pass grade of 18 is required. The maximum grade is 31.

The exams are the same throughout Italy and take place simultaneously.

Students have two exam sessions per course (November 20, 2025, 11:00 a.m. and December 10, 2025, 11:00 a.m.) and may retake each exam once.

Teaching tools

Teaching materials will be made available directly within the Zoom space used for participation. Additional activities are planned for the weeks of November 10-14 and December 1-5.

Office hours

See the website of Paola Taddei

See the website of Antonello Lorenzini

See the website of Michele Di Foggia

See the website of Silvia Cetrullo