Teaching code

4S008288

Credits

6

Coordinatore

Roberto Fiammengo

Language

Italian

Scientific Disciplinary Sector (SSD)

CHIM/06 - ORGANIC CHEMISTRY

Moodle Seminars

The teaching is organized as follows:

Learning objectives

The course aims to provide students with basic knowledge about organic synthesis focusing on biologically active molecules with special attention to the implementation of sustainable chemistry concepts. Course topics are: retrosynthetic analysis in the planning of organic syntheses; fundamentals of stereochemistry, stereoselective reactions, and asymmetric catalysis; peptide synthesis; synthesis of nucleic acids and basics of combinatorial chemistry; synthesis of peptide and nucleic acid analogs and derivatives; bioconjugation reactions and biofunctionalized nanomaterials.

Prerequisites and basic notions

The student must have learned and understood the basics of organic chemistry. In particular the student must be able to identify the functional groups in a molecule and have knowledge of their reactivity.

Program

- Course introduction: The importance of organic synthesis to prepare bioactive molecules. Introduction to synthetic strategies, conversion of functional groups, and protecting groups.
- Retrosynthetic analysis as a tool to plan organic synthesis. Fundamental of stereochemistry, stereoselective reactions, and asymmetric catalysis. The effect of stereoisomerism on biological activity.
- Synthesis of amino acids and peptides in solution and on solid phase: protecting groups for peptide synthesis; orthogonal protecting group strategies; formation of the peptide bond: activation and coupling methods; fragment condensation synthesis. Examples of bioactive peptide synthesis; examples of peptide synthesis with non-proteinogenic amino acids.
- Chemical synthesis of oligonucleotides: phosphodiester, phosphotriester, phosphoramidite, and H-phosphonate approaches. Protecting groups, purification strategies, and characterization methods.
- Introduction to the synthesis of oligonucleotide analogs, peptide nucleic acids (PNA)
- Bioconjugation reactions for the labeling of biological molecules; the concept of click-chemistry; preparation of antibody-drug conjugates.
- Introduction to nanoparticles. Design of nanoparticles for biomedical applications, nanoparticle biofunctionalization and characterization. Examples of drug and vaccine candidate formulations based on nanoparticles.

The listed topics are provisional. The program may undergo small changes during the semester.

Bibliography

Didactic methods

Lectures, case studies, exercises and group work in the classroom. Attendance to lessons is strongly recommended. The course also includes laboratory exercises whose attendance is mandatory.

Learning assessment procedures

The written exam consists of multiple-choice and open-ended questions, and exercises. The duration of the exam is between 90 and 120 minutes. Only in case the student has passed the written exam, he/she may ask the instructor for a complementary oral exam, which will last between 20 and 30 minutes.
For the laboratory part, the students are requested to prepare short critical reports about the performed experiments.

Evaluation criteria

Critical reasoning skills; competence in the use of specialized/technical jargon; conciseness, linearity and effectiveness of the exposure.
Marks out of thirty: written exam up to a maximum of 27/30; laboratory reports up to a maximum of 3/30; oral exam (optional, only if written exam ≥18/30) up to a maximum of 3/30.

Criteria for the composition of the final grade

Exam mark plus laboratory reports mark

Exam language

italiano e inglese (alcuni testi tecnici)