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Facoltà di Scienze Agrarie e Alimentari Università degli Studi di Milano
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Structure and functions of biomolecules: Structure and functions of biomolecules
Codice: G6403A
Docente:  Andrea Pinto
Anno di corso: 
Quadrimestre/semestre: 
CFU: 
Articolazione dei CFU: Lezioni frontali: 4
Obiettivi formativi:  The aim of the course is an in-depth discussion of the structure-activity relationships of the main classes of biological molecules. Strategies for synthesis, isolation and structural characterization of biomolecules will be treated. Potential applications in biotechnology will also be discussed, particularly those more closely related to the concept of bioeconomy.
Competenze acquisite:  The student will be able to critically discuss the structure-activity
relationships of the molecular classes presented in the course. He
will also acquire knowledge and skills on the most important
extraction, preparation/purification and structural characterization
methodologies. Finally, the student will be able to use the main
experimental and computational methodologies for understanding
the mechanisms of macromolecule-ligand interaction.
Sintesi del programma:  A general review on structure and chemistry of the main classes
of biomolecules: aminoacids and peptides, carbohydrates,
nucleic acids and lipids. In particular, the course deals with
advanced and up-to-date synthetic methods in solution and in
the solid phase. In addition, case studies on specific
biomolecules (e.g. insulin) and selected topics will be treated. In
addition, the course provides a general introduction to the main
spectroscopic techniques for chemical structural analysis of small
organic molecules and biomolecules: UV-Vis spectroscopy,
chiroptical methods, Nuclear Magnetic Resonance. Particular
emphasis is dedicated to practical aspects and applications in
structural biology (secondary and tertiary structural analysis,
solution structure of small proteins and oligonucleotides,
structure-activity relationship studies) and in the food and
biotechnology industry (process control).
Programma:  Teaching unit 2: “Structure and function of biomolecules” (Teacher: Prof. A. Pinto)
- Amino acids and peptides. 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 racemization phenomena and mechanisms. Methods of solid phase synthesis. Resins and cleavage conditions. Fundamentals of Amino acid biosynthesis and metabolism. Amino acids as biosynthetic precursors. Primary structure determination of proteins.
- Carbohydrates. Structure, properties, nomenclature. Anomeric effect. Oxidation and reduction reactions. Glycosylation reactions: concept of glycosyl donor and glycosyl acceptor, promoters, protecting groups. Chemo-enzymatic synthesis of glycosidic bond. Oligosaccharide and glycoconjugates synthesis on solid phase. Structural polysaccharides: cellulose and chitin. Storage polysaccharides: starch and glycogen. Carbohydrates as renewable raw material for fine chemicals.
- Nucleic acids. Structure, properties and nomenclature. Nucleosides and nucleotides. Purine and pyrimidine heterocycles. DNA bases. Acid-base characteristics, tautomeric forms, and reactivity. Nucleosides: structure and biological properties. Phosphate, pyrophosphate and triphosphate esters. Nucleotides. Nucleic acids. Polynucleotide structure. Chemical stability and main reactions of DNA and RNA: hydrolysis, oxidation and alkylation. Chemical sequencing of DNA and its scope of use. Chemical synthesis of DNA, protector groups, phosphoramidite, H-phosphonate method. RNA chemical synthesis. Modified nucleic acids and mimics.
- Lipids. Structure and properties. Lipid classification. Auto-oxidation and photo-oxidation reactions. Synthesis of complex lipids: some examples. Phospholipids and glycolipids. Micelles and liposomes. Main classes of non-saponifiable lipids.
Prerequisiti:  Basic knowledge of the structure and nomenclature of the main functional groups in organic chemistry. Basic knowledge of biochemistry. For any question and further details please contact the teacher at enzio.ragg@unimi.it or andrea.pinto@unimi.it.
Propedeuticità:  none
Materiale didattico:  a) E. Rossi, D. Nava, G. Abbiati,G. Celentano,S. Pandini “Structure
determination of organic compounds, practical exercise” Ed.
EdiSES;
b) Biochemistry- 4th Edition – Voet & Voet –Wiley;
c) Organic Chemistry - 4thEdition - Clayden, Greeves, Warren and
Wothers-Oxford University Press, Wiley and Sons;
d) Slides of lessons available through the Ariel Web Site
Modalità d'esame e altre info:  MODALITÀ DI ESAME ED ALTRE INFORMAZIONI: The
examination is in the written form and will deal with all topics
inherent to both course units. Unit 1: a) the student should be
able to describe the structure of a simple organic molecule on
the basis of the provided spectroscopic data; b) a theoretical
question about general aspects of molecular spectroscopy. Unit
2: two questions related to synthetic aspects and the description
of structure-activity relationships of specific classes of
compounds described in the course. Students should answer to
all questions within 2 hours. To each question a formal maximum
value of 8 points will be assigned. The exam is considered
sufficient when at least 9 points for each unit have been
assigned. At least 7 exam sessions per year will be guaranteed.
The date of the exam will be published on SIFA platform.
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Programma di Structure and functions of biomolecules: Structure and functions of biomolecules (versione in pdf)
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