Lecturer: Piercarlo Mustarelli   Dario Pasini  

Course name: Organic Chemistry and Biomaterials
Course code: 503201
Degree course: Bioingegneria
Disciplinary field of science: ING-IND/34 - CHIM/06
University credits: CFU 12
Course website: n.d.

Specific course objectives

The course introduces to the students the principles of Organic Chemistry and Biomaterials. The course will be organized in an initial module of Organic Chemistry (3 credits) and in a module of Biomaterials (6 credits). Regarding the Organic Chemistry module, the objective of the course is to give bioengineers the necessary basis for the understanding of the structure and reactivity of organic compounds, which they will frequently encounter during their studies. The aim of the second module is to convey the concept of biomaterial and its fundamental and growing importance in medicine. Moreover, illustration of the major technical study of the surfaces of biomaterials will also be useful to provide students with a basic knowledge of the techniques of choice used in the laboratory practice.

Course programme

Module of Organic Chemistry
In the Organic Chemistry module the fundamental concepts of Organic Chemistry will be illustrated (structure and bonding, acidity and basicity, resonance, stereoisomery and chirality). The structure of the main classes of organic compounds will be illustrated (saturated and unsaturated hydrocarbons, aromatic compounds, alcohols and ethers, aldehydes and ketones, amines and carboxylic acids) and their reactivity will be described considering the characteristic functional groups of each class. The main classes of biomolecules will be examined: aminoacids and proteins, carbohydrates, lipids, nucleic acids. Organic polymers and the most important polymerization reactions will be introduced. The program is enucleated in detail: Structure and bonding. Electronic structures of atoms. Lewis structures. Electronegativity and chemical bonds. Ionic, covalent and noncovalent bonds. Formal charge. Resonance. Functional groups. Bronsted-Lowry acids and bases. Lewis acids and bases. Stereoisomery and chirality. Definitions. Stereocenters. The R,S system. Molecules with two or more stereocenters. Enantiomers and diastereoisomers. Optical activity. Polarized light. Racemic mixtures. Separation of enantiomers. Types of organic reactions. Mechanisms, equilibrium, kinetics and free energy profiles. Radicalic and polar reactions. Structure of alkanes. Constitutional isomerism and nomenclature. Conformation of alkanes and cycloalkanes. Unsaturated hydrocarbons. Structure and configuration of alkenes. Reactions of alkenes: electrophilic addition. Alkynes, dienes and polyenes. Alkyl halides and nomenclature. Nucleophilic substitution and elimination. Mechanisms. Aldehydes and ketones. Structure and nomenclature. Nucleophilic addition reactions. Acetals and emiacetals. Keto-enol tautomerism. Oxidation and reduction of aldehydes and ketones. Benzene and aromaticity. Nomenclature. Energy of resonance of benzene. Aromatic electrophilic substitution. Alcohols, phenols, ethers and thiols. Nomenclature. Acidity and basicity. Reactions of alcohols and phenols. Reactivity of epoxides and thiols. Amines and carboxylic acids. Structure, properties and nomenclature. Reactions with acids and bases. Esterification of carboxylic acids. Aminoacids. Isoelectric point. Polypeptides and proteins. Carbohydrates. Monosaccharides. Structure, nomenclature and stereoisomerism. Fischer and Haworth projections. Mutarotations. Disaccharides and polysaccharides. Structure of lipids, nucleic acids, nucleosides and nucleotides.

Module of Biomaterials
The module starts from the definition of biomaterial and biocompatibility. After a recall on the chemical bond, goes to the definition of solid state and the classification of the main classes of solids and their main defects. We then define the main mechanical and plastic properties of materials. Much of the course will be devoted to the main techniques of study of the surfaces of biomaterials (spectroscopic techniques, thermal, microscopic and contact angle measurements). Finally, we will address the main techniques of surface modification of biomaterials (silanization, chemical reactions, laser or plasma, self-assembling or Langmuir-Blodgett monolayers etc. ..) useful to modify the biocompatibility. The most important classes of biomaterials are then reviewed. 1) Polymers: categories, classification of physico-chemical and mechanic properties, polymerization methods, classes of interest as biomaterials. 2) Ceramics and glass-ceramics: traditional and advanced materials, synthesis methodologies, classes of interest (alumina, calcium phosphates, bioglasses, pyrolytic carbon). 3) Metals: phase diagrams, crystalline structures, metals and alloys, classes of interest (iron, steels, titanium alloys, tantalium, nichel, noble metals). Corrosion.

Course entry requirements

Notions of chemistry and physics acquired during the batchelor

Course structure and teaching

Lectures (hours/year in lecture theatre): 80
Practical class (hours/year in lecture theatre): 12
Practicals / Workshops (hours/year in lecture theatre): 0

Suggested reading materials

Riccardo Pietrabissa. Biomateriali per Protesi e Organi Artificiali. Patron. Textbook in Italian.

McMurry. Chimica organica: un approccio biologico. Zanichelli.

Testing and exams

Oral exam. The two modules can be given separately.