B029593 - ADVANCED SYNTHETIC METHODS

English

The aim of the course is the description of advanced synthetic methods used for the production of intermediates, natural substances, biologically active molecules.
Topics: Methods for the activation of the C-H bond; organocatalysis; photocatalysis; solid phase strategies for the synthesis of peptides and oligosaccharides; strategies for the macrocyclization of peptides for the stabilization of bioactive conformations; purification and characterization strategies.

Handout and bibliographic material proposed by the teachers

Knowledge and Understanding: The course aims to train students on modern synthetic approaches for the production of complex organic molecules.
Learning skills: Through the presentation of the different synthetic approaches and various application examples, the synthetic methodological bases will be provided.
Autonomy of Judgement: critical capacity in the choice of the synthetic approach and in adapting it to each specific situation.
Communication: ability to communicate with appropriate vocabulary the skills acquired during the course.

No

Lectures and laboratory training

No

Oral test in order to verify the knowledge, critical thinking, skills to use and develop advanced synthetic strategies for the production of complex molecules or materials.

Aims: The aim of the course is the description of advanced synthetic methods used to produce intermediates, natural and modified biologically active molecules. The most important modern synthetic strategies will be presented covering classical solution and solid-phase strategies applied to peptides, proteins, and saccharides.
Lectures
Modern synthetic methods for the formation of C-C bond: metathesis of alkenes and alkynes, cross coupling reactions, enantioselective aldol condensations, stereoselective synthesis. Synthetic methods for C-H bond activation. Principles and applications to organocatalysis. and photocatalysis.
Solid-phase strategies for the synthesis of peptides and oligosaccharides: orthogonal protecting and activating groups. Strategies for macrocyclization to stabilize bioactive conformations, such as stapled peptides (dicarba- and clicked peptides, etc.) for biomedical applications (R&D of peptide drugs and diagnostics) and development of biomimetic materials. Ligation strategies to implement the convergent assembly of complex peptides (i.e., glycopeptides, phosphopeptides, etc): from oligopeptides to co- and post-translationally modified proteins, such as glycoproteins (native and aberrant). Semi-synthetic strategies to obtain homogeneous glycoproteins using specific enzymes. Efficient purification and characterization strategies.
Laboratory practice: each student will choose one of the following activities that will be performed in a research laboratory.
Use of organocatalysis for the preparation of bioactive molecules. Use of photocatalysis for the preparation of synthetic intermediates. Preparation of monomers for the production of materials for energy through the formation of C-C bond and C-H activation.
Synthesis of a modified peptide (glyco, lipo, phosphopeptides) and development of ligation strategies to obtain homogenous complex proteins also by semi-synthetic strategies.
Preparation and characterization of an oligosaccharide.