CODE 60828 ACADEMIC YEAR 2016/2017 CREDITS 8 cfu anno 2 CHIMICA E TECNOLOGIA FARMACEUTICHE 8451 (LM-13) - SCIENTIFIC DISCIPLINARY SECTOR CHIM/06 LANGUAGE Italiano TEACHING LOCATION SEMESTER 2° Semester PREREQUISITES Propedeuticità in ingresso Per sostenere l'esame di questo insegnamento è necessario aver sostenuto i seguenti esami: Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) GENERAL AND INORGANIC CHEMISTRY (PCT)(MD) 55401 2015 ORGANIC CHEMISTRY I (PCT)(MD) 60822 2015 Propedeuticità in uscita Questo insegnamento è propedeutico per gli insegnamenti: Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) GENERAL PHARMACOLOGY AND TOXICOLOGY (PCT MD) 64200 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) BIOCHEMISTRY AND APPLIED BIOCHEMISTRY (I.C.)(PCT MD) 80520 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) PHARMACEUTICAL TECHNOLOGY AND LAW II (WITH PRACTICE)(PCT MD) 67615 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) PLANT BIOACTIVE COMPOUNDS (PART OF I.C.)(PCT MD) 80449 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) PLANT BIOLOGY (PART OF INTEGRATED COURSE)(PCT MD) 80448 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) PLANT BIOLOGY AND BIOACTIVE COMPOUNDS (I.C.)(PCT MD) 80447 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) APPLIED MEDICINAL CHEMISTRY (MD) 67617 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) MEDICINAL AND TOXICOLOGICAL CHEMISTRY I (PCT MD) 80446 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) TECHNOLOGY AND PHARMACEUTICAL LAW I (PCT MD) 67569 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) PHARMACOLOGY AND PHARMACOTERAPY (PCT MD) 67563 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) FOOD CHEMISTRY (PCT MD) 64194 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) PHARMACEUTICAL AND TOXICOLOGICAL CHEMISTRY II (PCT MD) 67558 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) SINTESI DEI FARMACI (CON ESERC.) 80453 Pharmaceutical chemistry and technology 8451 (coorte 2015/2016) COSMETIC PRODUCTS 67501 AIMS AND CONTENT LEARNING OUTCOMES Further insight into the reactivity of organic molecules through the study of difunctional molecules. Carbon-carbon bond forming reactions with particular emphasis on the costruction of cyclic systems. Heterocycles. Natural organic substances. TEACHING METHODS The lessons are given in the traditional way (64 hours in the classroom). The attendance is compulsory. Only those students who have attended at least 60% of the lessons are admitted at the exam. SYLLABUS/CONTENT FURTHER INSIGHT INTO THE REACTIVITY AND PREPARATION OF BIFUNCTIONAL COMPOUNDS (24 hours, Prof. Banfi) A1 Polyunsaturated and polycyclic systems and bicarboxylic compounds A1.1 Conformations of cycloalkanes and bicycloalkanes A1.1.1 Conformations of monocyclic alkanes A1.1.2 Conformation of fused bicyclic alkanes A1.1.3 Nomenclature and properties of bridged bicyclic systems A1.2 Dienes A1.2.1: Conjugation and UV-visble absorption A1.2.2: Electrophilic addition to conjugated dienes A1.2.3: Pericyclic cycloadditions: the Diels-Alder reaction A1.2.4 Ring-closing metathesis A1.2.5 Allenes A1.3 Bicarboxylic acids A1.4 Aromatic polycyclic ystems A1.4.1: Nomenclature and properties A1.4.2: Fullerenes, graphite, graphene, carbon nanotubes A1.4.3: Arene oxides A1.4.4: Electrophilic substitutions on naphthalene A1.5 Biaryl systems A1.5.1 Chirality in biaryls A1.5.2 Suzuki reaction for the synthesis of biaryls and dienes A2 Compounds with two oxygenated functions or one oxygenated functiona and an unsaturation A2.1 Conjugated carbonyl and carboxylic compounds A2.1.1 Preparation through: halogenation/elimination, crotonic condensation, Knoevenagel reaction; intramolecular metathesis; Wittig and Horner-Wadsworth-Emmons reactions A2.1.2 Synthetic equivalence A2.1.3 Conjugated nucleophilic additions: reactions with mild nucleophiles, with organometallic reagents, with hydrides, Michael reaction. A2.1.4 Robinson annulation A2.1.5 Conjugated additions in biology A2.1.6 Conjugated additions and other reactions of enamines A2.2 1,3-Dioxygenated compounds A2.2.1: Cross aldol reactions with enolate preformation A2.2.2: Cross alsol reactions with synthetic equivalents of aldehydes A2.2.3 Oxidations with diacetoxyiodobenzene and Swern oxidation A2.2.4 Claisen and Dieckmann condensations A2.2.5 Aldol additions and Claisen condensations in biology A2.3 1,2-Dioxygenated compounds A2.3.1 Retrosynthetic strategies: logical and illogical disconnections A2.3.2 Cyanide anion as acyl anion equivalent A2.3.3 Isocyanides: Passerini reaction A2.3.4 Dithianes A2.3.5 1,2-Diols A2.3.6 Cyclic acetals A3) Radical reactions, phenols, quinones A3.1 Radical reactions A3.1.1: Generality A3.1.2: Radical polymerizations A3.1.3 Autooxidations A3.1.4 Anti-oxidants A3.2 Phenols as natural anti-oxidants A3.3 Quinones HETEROCYCLIC COMPOUNDS (21 h, Prof. Petrillo). Classification and nomenclature of heterocyclic compounds Electronrich aromatic heterocycles General features Synthesis and reactivity of pyrrole, furan, thiophene and related benzo-fused compounds Electronpoor aromatic heterocycles General features Synthesis and reactivity of pyridine, quinoline, isoquinoline,pyrimidine, pyrazine, pyridazine Aromatic penta-atomi heterocycles with two heteroatoms General features Synthesis and reactivity of imidazole, oxazole, isoxazole Saturated strained heterocycles: structure, synthesis and reactivity of oiranes, aziridines, oxetanes, azetidines BIOMOLECULES (19 h, Prof. Riva). C1 Carbohydrates C1.1 Monosaccharides C1.1.1 Stereochemical families C1.1.2 Fischer and Haworth formulas, pyranose and furanose conformations C1.1.3 Anomeric effect C1.1.4 Mutarotation C1.1.5 Behaviour of monosaccharides in acids and in bases C1.1.6 Reduction and oxidation reactons; reducing sugar assays C1.1.7 Glycosides: structure, properties and synthesis of simple glycosides C1.1.8 Synthetic strategies for the synthesis of complex glycosides through chemical means (use of protecting groups and activation of glycosy donor). Enzymatic synthesis C1.1.9 Osazones C1.1.10 Kiliani-Fischer synthesis C1.1.11 Ruff and Wohl degradations C1.1.12 Determination of relative and absolute configuration of main monosaccharides C1.2 Disaccharides: maltose, cellobiose, saccharose and lactose C1.3 Polysaccharides: structure and properties of main polysaccharides (starch, glycogen, cellulose, chitin, pectin, hyaluronic acid) C1.4 Antigene determinants of cells; blood groups C1.5 Glycoconjugates C1.5.1 glycolipids C1.5.2 glycoproteins C2 Lipids C2.1 Fatty acids and derivatives (amides, waxes) C2.2 Eicosanoides (prostaglandins etc.) C2.3 Glycerolipids (triglycerides: fats, oils) C2.4 Soaps and tensioactive compounds C2.5 Glycerophospholipids C2.6 Sphingolipids C2.7 Terpenes, Terpenoids and their biosynthesis C2.8 Steroids C3 Amminoacids C3.1 Nomenclature C3.2 Structure and classification C3.3 Acid-base properties C3.4 Isoelectric point C3.5 Synthesis of alpha-aminoacids (from alpha-haloacids, from acylaminomalonic esters, through reducing amination, through enantioselective reduction of alha-acylaminoacrylic acids, through Strecker reaction) C3.6 Resolution of racemic alpha-amminoacids C4 Peptides and proteins C4.1 Primary structure, secondary structure (alpha-helix, beta-sheet, random coil), tertiary and quternary structure C4.2 Protein denaturation C4.3 Determination of primary structure Through exhaustive hydrolysis coupled with ion exchange chromatography and visualization with ninhydrin Through Edman method Through use of cyanogen bromide Through enzymatic methods C4.4 Chemical synthesis in solution (from left to right and from right to left; use of protecting groups; activation of carboxylic function) and in solid phase (Merrifield resins) C5 Nucleic acids C5.1 Nitrogen bases C5.2 ZSugars C5.3 Nucleosides C5.4 Nucleotides C5.5 Oligonucleotides and Nucleic acids C5.6 Secondary and tertiary structure of DNA C5.7 Examples ofgenetic mutations RECOMMENDED READING/BIBLIOGRAPHY Chimica Organica AA. VV. a cura di B. Botta Edi-Ermes 2011 (p. 1174) Chimica Organica di Marc Loudon, EdiSES 2010 (p. 1374) Chimica Organica di McMurry, Piccin 2012 (p. 1262) Chimica dei Composti Eterociclici di D. Sica, F. Zollo - EdiSES (l'ultima edizione) Chimica degli Eterocicli di G. Broggini, G. Zecchi – vol. 1 LaScientifica (l'ultima edizione) TEACHERS AND EXAM BOARD LUCA BANFI Ricevimento: Luca Banfi is always present in the department from 8.30 to 13.00 and from 15.00 to 18.30. However, due to the many lessons and exams he is involved in and to the institutional meetings, it is impossible to establish in advance a time interval where he will be surely not engaged. Therefore students are pleased to take an appointment in advance by E-mail. They will be received in few days. RENATA RIVA GIOVANNI PETRILLO Exam Board LUCA BANFI (President) GIOVANNI PETRILLO (President) RENATA RIVA (President) LISA MONI CINZIA TAVANI LESSONS LESSONS START The lessons will begin february 20, 2017. Class schedule ORGANIC CHEMISTRY II (PCT)(MD) EXAMS EXAM DESCRIPTION There will be a preliminary written exam consisting in 12 questions. The students will have 90 minutes for answering. The written exam will be followed, the same day, by an oral exam. At least one question for each of the three parts will be asked at the oral. Only the students who get a sufficient grade at the written exam will be admitted to the oral. The oral exam must be given the same day than the written one and if a student fails to pass the oral, will have to repeat also the written part. In general, the grade of the written exam in not influential on the final vote. Only in particular cases, when the written exam has a very high mark, it can positively influence the final grade. ASSESSMENT METHODS The oral exam is always carried out by three members of permanent teaching staff and lasts at least 45 minutes (15 minutes for each professors). The students will demonstrate to have reached a suffidient knowledge both by answering to questions, and by drawing at the blackboard formulas, reaction equations, mechanisms and so on. Therefore, also taking into account the preliminary written part, the commission is definitely able to verify, with high accuracy, the fullfilment of learning outcomes. If the commission decides that the learning outcomes have not been met, the student will be invited to try again the exam in a following date. Exam schedule Data appello Orario Luogo Degree type Note 15/06/2017 09:00 GENOVA Scritto + Orale 29/06/2017 09:00 GENOVA Scritto + Orale 13/07/2017 09:00 GENOVA Scritto + Orale 06/09/2017 09:00 GENOVA Scritto + Orale 20/09/2017 09:00 GENOVA Scritto + Orale 23/01/2018 09:00 GENOVA Scritto + Orale 08/02/2018 09:00 GENOVA Scritto + Orale FURTHER INFORMATION Only the students who have already passed Organic Chemistry are admitted to the exam. The professors will check the observance of this rule just before the written exam.
