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Advanced synthetic methods

Stefano Cicchi and Anna Maria Papini

6 ECTS: 32 hours of lectures and 24 hours of laboratory practice

Aims: The aim of the course is the description of advanced synthetic methods used to produce intermediates, natural and modified biologically active compounds. The most important modern synthetic strategies will be presented covering classical solution and solid-phase methods 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 the C-H bond activation. Organocatalysis: principles and applications. Photocatalysis: principles and applications.

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 analogs, clicked peptides, etc.) for biomedical applications (R&D of drugs and diagnostics) and development of biomimetic materials ligation. Ligation strategies and implementation in the convergent assembly of complex peptides (i.e., glycopeptides, phosphopeptides, etc): from oligopeptides to co- and post-translationally specifically 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, phospho-) and example of a ligation strategy to obtain homogenous complex proteins also by semi-synthetic strategies.

Preparation and characterization of an oligosaccharide target.

Last
update

31.05.2023

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