Synthesis of bioactive molecules (2020/2021)

Course code
4S008288
Name of lecturer
Roberto Fiammengo
Coordinator
Roberto Fiammengo
Number of ECTS credits allocated
6
Academic sector
CHIM/06 - ORGANIC CHEMISTRY
Language of instruction
Italian
Location
VERONA
Period
I semestre dal Oct 1, 2020 al Jan 29, 2021.

Lesson timetable

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Learning outcomes

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 and physical methods for their characterization (NMR, IR, Circular Dichroism); synthesis of nucleic acids and basics of combinatorial chemistry; synthesis of peptide and nucleic acid analogs and derivatives; bioconjugation reactions and biofunctionalized nanomaterials. The course includes a practical to allow students to practice and develop manual skills in the synthesis of molecules with biological activity.

Syllabus

The listed topics are provisional. The program may undergo changes during the semester.
- 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. Brief overview of the structural characterization of peptides (NMR, IR, circular dichroism).
- 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.

Reference books
Author Title Publisher Year ISBN Note
Andrew B. Hughes Amino Acids, Peptides and Proteins in Organic Chemistry: Building Blocks, Catalysis and Coupling Chemistry, Volume 3 Wiley‐VCH Verlag GmbH & Co. KGaA 2011 9783527631803 Libro disponibile attraverso Universe
Andrew B. Hughes Amino Acids, Peptides and Proteins in Organic Chemistry: Volume 4: Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis, Volume 4 Wiley‐VCH Verlag GmbH & Co. KGaA 2011 9783527631827 Libro disponibile attraverso Universe
Greg T. Hermanson Bioconjugate Techniques (Edizione 3) Elsevier 2013 978-0-12-382239-0
Ravin Narain Chemistry of Bioconjugates: Synthesis, Characterization, and Biomedical Applications John Wiley & Sons, Inc. 2014 9781118775882 Libro disponibile attraverso Universe
Piet Herdewijn Oligonucleotide Synthesis Humana Press 2005 978-1-59259-823-6

Assessment methods and criteria

The course will be concluded with an examination where the student demonstrates proficiency in the subject matter of the course, according to the specified “Learning outcomes”. The written examination consists in multiple-choice and open-ended questions. The student may ask the instructor for a complementary oral test after having passed the written test.