The student will acquire intellectual tools of bioorganic chemistry to investigate by a chemical approach biochemical functions and influencing 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.
Notes and articles will be made available by the teacher.
Learning Objectives
The course has the target to introduce students to advances in the field of contemporary bioorganic chemistry, emphasizing the application of chemical approaches to interrogate biochemical function 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.
Prerequisites
Courses required: Organic Chemistry I and Organic Chemistry II
Courses recommended: none
Teaching Methods
Presentations based on slides. Instructional strategy based on flipped classrooms. Exchange of material via dropbox.
Further information
.
Type of Assessment
Oral examination.
Course program
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.
Application of peptides and proteins
Peptide pharmaceuticals. Peptide diagnostics. New peptide-based diagnostic assays.