CHIM/06 (ORGANIC CHEMISTRY)
DEPARTMENT OF BIOLOGY AND BIOTECHNOLOGY "LAZZARO SPALLANZANI"
2nd semester (01/03/2022 - 14/06/2022)
48 lesson hours
Basic knowledge of Organic Chemistry
The aim of the course is to provide adequate knowledge of the chemistry of biomolecules. The course, organized by type of compound, will focus attention on:
- properties and reactivity of biologically relevant organic molecules (carbohydrates, amino acids and peptides, lipids, nucleic acids).
- modification of their structure, synthesis of derivatives and mimics.
- their application in different fields of science.
Overview of stereochemistry. Insights into the concepts of isomerism, structural (constitutional) and stereoisomerism (enantiomers and diastereomers). Topical relationships between atoms or groups of atoms: homotopic, enantiotopic, diastereotopic groups; stereochemical descriptors pro-R, pro-S, Re, Si. Importance of chirality in biological systems.
Amino acids and their side chains. Basicity and acidity of ionizable groups in the side chains. pKa and isoelectric point of amino acids. metabolism of amino acids.
Modern solid phase synthesis methods. Resins and release conditions. Methods of activation and conjugation. Possible racemization phenomena.
Carbohydrates. Monosaccharides. Structure, nomenclature, stereoisomerism. Anomeric effect. Reactivity of monosaccharides.
Glycosylation reactions: concept of glycosyl donor and glycosyl acceptor, promoters, protecting groups.
Synthesis of polysaccharides. Synthesis of the glycosidic bond by enzymatic way. Synthesis of oligosaccharides and glycoconjugates on solid phase.
Aromaticity review: Benzene and heterocycles.
Hexatomic and pentatomic heterocycles, pyrimidines and purines.
Structure and properties. Synthesis. Modified nucleic acids and mimics.
Antigen and antisense strategies. Interactions between nucleic acids and various molecules. Nucleic acids as a smart material for nanotechnology.
Lipids and steroids. Structure and properties. Auto-oxidation reactions. Examples of synthesis of complex lipids. Self-assembly processes of lipids: bilayers, micelles, vesicles, liposomes.
Reccomended or required readings
Specific notes are provided in electronic format.
Reference text: Brown-Poon, Organic chemistry EdiSES.
Recommended reading: Amino Acid and Peptide Synthesis, John Jones, Oxford press. Carbohydrate Chemistry, B. G. Davis and A. J. Fairbanks, Oxford press. Nucleic Acids Book - Chemistry and Biology of Nucleic Acids.
The student must demonstrate that they have acquired and assimilated the basic concepts presented during the course by passing a written test.