Learning outcomes of the course unit
Acquisition of knowledge on th moleular structure and of chemical and biological properties of bio-macromolecules: lipids, peptides, carbohydrates and nucleic acids. Synthetic methodologies of natural and unnatural biopolymers: peptides, saccharides and oligonucleotides. Introduction to pre-biotic chemistry.
Course contents summary
Lipids. Principal classes of lipids. Triglycerides and their chemical properties. Autooxidation and photooxidation of fatty acids. Phospholipids and glycolipids. Micelles and liposomes. Principal classes of non-saponifiable lipids.
Peptides. Nomenclature. Cis-trans isomers of the peptide bond bond. Acid-base properties of peptides, isoelectrivc point. Hydrolysis. Characterization, purification and sequencing. Peptide synthesis: protecting groups, activation, methods in solution and on solid phase; Boc and Fmoc strategy. Conjugated peptides, cyclic peptides, peptido-mimetics. Combinatorial chemistry applied to peptide libraries.
Carbohydrates. Monosaccharides. Stereoisomery, linear and ciclic conformations, alfa and beta configurations, mutarotation. Reduction, oxidation, rearrangements. Tollens and Fehling reactions, reactions with amines, alcohols; glycoside formation. Hydrolysis of glycosides. Reaction of the monosaccharides. Examples of biologically relevant glycosides and glycoproteins. Oligo- and Polisaccharides. Reactivity. Structure determination. Examples of biologically relevant disaccharides and oligosaccharides Cyclodextrin: structure and applications. Synthetic oligosaccharides. Polysaccharides: classification and structure of biologically relevant structures.
Nucleosides and Nucleotides. Pyrimidine and purine heterocycles, nucleobases and their properties. Acid base properties, tautomerism, reactivity. Nucleosides: structure and biological properties. Phosphor derivatives and their reactivity. Nucleotides. Nucleic acids. Polynucleotide structures. Double helices and factors affecting their stability: hydrogen bonds, hydrophobic effect, stacking, electrostatic repulsion. DNA chemical synthesis: protecting groups, phosphoramidite, H-phosphonate methods. Chemical synthesis of RNA. Stability of DNA and RNA to hydrolysis. DNA reactivity: alkylating agents, interacalating agents, cross-linking, oxidations, photoactivation. Chemical DNA sequencing and comparison with present sequencing technologies.
Antigene and antisense oligonucleotides, modified oligonucleotides.
W.H. Brown; Introduzione alla Chimica Organica-terza Edizione. Edises, 2005. Chapt 10, 14, 15,19, 20, 21, 18, 19.
W.H. Brown, C.S.Foote, B.L.Iverson E.V. Anslyn. Chimica Organica. IV Edizione EdiSES (2009).Capitoli 17, 18, 23, 26, 27, 28.
K. P. Vollhardt, N.E. Schore :Chimica Organica. terza edizione Zanichelli Editore, 2005. Chapt. 19,20,21,24,25,26
P.Y. Bruice Chimica Organica. Edises, 2005. chapt 17, 21, 23, 26, 27.
J. McMurry :Chimica Organica. 7 Edizione. Piccin 2008. chapt 20, 21, 24, 26, 27, 28.
Lecture notes provided by the teacher
V. Santagada, G. Caliendo :Peptidi e Peptidomimetici. PICCIN Editore, 2003.
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
Assessment methods and criteria
Written and oral examination integrated with other modules
Integrated course with other two modules: Analytical Chemistry and Bioinorganic Chemistry