The aim of the course is to give an adequate knowledge of
- 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
Organic Chemistry 1 and 2
Course contents summary
Chemico-physical properties and reactivity of carbohydrates, amino acid and peptides, lipids and nucleic acids.
Modification of their structure and synthesis of corresponding oligomers.
Use as raw material for the production of chemicals.
Noncovalent interaction with molecular and macromolecular species.
Amino acids and peptides
Why to synthesize a peptide. Structure and properties of amino acids and peptides. Nitrogen protecting groups: insertion and removal. Possible secondary reactions. Protecting groups of carboxylic and hydroxyl groups. Methods for activation and coupling. Possible racemisation phenomena and mechanisms. Methods of solid phase synthesis. Resins and cleavage conditions.
Role of carbohydrates in non metabolic biological processes. Structure, properties, nomenclature. Anomeric effect. Oxidation and reduction reactions. Glycosylation reactions: concept of glycosyl donor and glycosyl acceptor, promoters, protecting groups. Enzymatic synthesis of glycosidic bond. Oligosaccharide and glycoconjugates synthesis on solid phase. Synthesis of glycosidic clusters and concept of multivalency and glycoside cluster effect. Carbohydrates as renewable raw material for fine chemicals.
Structure and properties. Synthesis. Modified nucleic acids and mimics. Antigene and antisense strategies. DNA and RNA binders. Nucleic acids as smart material for nanotechnology
Structure and properties. Autooxidation reactions. Synthesis of complex lipids: some examples. Self-assembly of lipids: double layers, lamellar phases, vesicles, liposomes. Delivery applications. Determination of size and zeta potential by DLS. Investigation through AFM and TEM
V. Santagada, G. Caliendo: Peptidi e Peptidomimetici. PICCIN Editore.
S. M: Hecht. Bioorganic Chemistry: Nucleic Acids. Oxford University Press.
S. M: Hecht. Bioorganic Chemistry: Peptides and Proteins. Oxford University Press.
S. M. Hecht: Bioorganic Chemistry: Carboydrates. Oxford University Press
B. Ernst, G.W. Hart, P. Sinay: Carbohydrates in Chemistry and Biology; Vol.1, Wiley-VCH.
M. Demeunynck, C. Bailly, W.D. Wilson: DNA and RNA binders; Wiley-VCH.
R.S. Dias, B. Lindman: DNA interactions with polymers and surfactants; Wiley.
Papers from the literature.