B012895 - BIOORGANIC CHEMISTRY

Italian and if required by all the students the course will be delivered in English

The student will acquire intellectual tools of bioorganic chemistry to investigate by a molecular approach, biochemical functions in order to influence biological processes. The multidisciplinary approach will be presented by synthetic strategies of peptides and proteins bearing co- and post-translational modifications as key molecules in cell-cell recognition events leading to understand fundamental problems at the interface between chemistry and biology.

The teacher will provide electronic material and scientific articles.

The course has the target to introduce students to advances in the field of contemporary bioorganic chemistry, i.e;, chemical biology, emphasizing the application of chemical approaches to interrogate biochemical functions and influence fundamental biological processes. A multidisciplinary approach, involving synthetic strategies to peptides and proteins co- or post-translationally modified, as key molecules involved in cell-cell recognition events, will be addressed to understand fundamental problems at the interface of chemistry and biology.

Courses required: Organic Chemistry I and Organic Chemistry II

Courses recommended: Chemistry of Biomolecules

Presentations based on slides. Instructional strategy based on flipped classrooms. Exchange of material via Google Drive.

In case of lockdown the course will be delivered online via Google Meet.

Intermediate tests
a) Four scientific articles will be selected from the literature for each subject afforded during the frontal lessons. The student shall prepare a power point presentation to discuss the subjects in the context of the class.
b) Laboratory activity to learn the following techniques:
i) synthesis and characterisation of peptide and/or protein materials for nutraceutics, cosmeceutics, drug and diagnostics development
c) Intermediate test with a practical or virtual activity

Final oral examination: the student will be asked to answer questions on the subjects afforded during the course.

Fundamental chemical and structural principles
Definitions and main conformational features of the peptide bond. Building blocks. Classification and nomenclature. Analysis of the covalent structure of peptides and proteins. Three-dimensional structure. Methods of structural analysis.
Biologically active peptides
Occurrence and biological roles. Biosynthesis. Selected bioactive peptide families.
Peptide Synthesis
Principles and objectives. Protection of functional groups. Peptide bond formation. Racemisation during synthesis. Solid Phase Peptide Synthesis. Biochemical synthesis
Synthesis concepts for peptides and proteins
Strategy and tactics. Synthesis in solution. Optimised strategies on polymeric support. Ligation of unprotected peptide segments.
Synthesis of special peptides and peptide conjugates
Cyclopeptides. Cystine peptides. Glycopeptides. Phosphopeptides. Lipopeptides. Sulfated peptides.
Peptide and protein design, pseudopeptides, peptidomimetics
Peptide design. Modified peptides. Peptidomimetics. Macropeptides and de novo design of peptides and proteins.
Combinatorial synthesis
Parallel synthesis. Synthesis of mixtures.
Industrial application of peptides and proteins in nutraceutical and cosmeceutical sciences.
Peptide drugs. Peptide-based diagnostics. New peptide-based diagnostic assays.