CHEMISTRY OF NATURAL ORGANIC SUBSTANCES
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- Versione italiana
- Academic year
- 2022/2023
- Teacher
- DANIELA PERRONE
- Credits
- 6
- Didactic period
- Secondo Semestre
- SSD
- CHIM/06
Training objectives
- The purpose of the course is to provide students with an overview on the structure, biosynthesis and biological role of the most important classes of natural organic compounds.
Main knowledge acquired:
main knowledge gained will cover strategies and reaction mechanisms used by the "Nature" for the biosynthesis of various classes of secondary metabolites such as fatty acids, polyketides, terpenes, steroids, phenols, lignans, flavonoids and alkaloids.
Main skills acquired:
at the end of the course the student will acquire the ability to identify the main classes of natural organic substances and will be able to understand the main biosynthetic pathways leading to the production of secondary metabolites. The student may also predict the course of a specific reaction by structure-reactivity correlation. Prerequisites
- The students should have a good knowledge of basic organic chemistry.
Course programme
- Primary and secondary metabolism and metabolites; the main pathways of the secondary metabolism, the building blocks of the secondary metabolism (3 h)
The construction mechanisms, alkylation reactions: nucleophilic substitution and electrophilic addition; aldol and Claisen reactions (3 h); synthesis of imines and Mannich reaction; amino acids and transamination, decarboxylation reactions (3 h)
Stereochemistry of biomolecules: stereoisomers, racemic mixtures, meso-compounds, stereoselective and stereospecific synthesis, chirality and prochirality center (3 h)
Enzymes: structure and definition; international classification of enzymes, mechanisms of action, catalytic site (3 h); chemistry of the enzymatic catalysis (acid-base catalysis, covalent catalysis, electrophilic catalysis); cofactors (essential ions and coenzymes): ATP, NADPH, FAD, FMN, SAM, DMAPP, IPP, acetyl-CoA, PLP, TPP and lipoic acid (3 h)
The acetate pathway: fatty acids and polyketides; fatty acid characteristics and biosynthesis; fatty acid synthase (type I and II FAS), structure of the homodimeric type I mammalian FAS and synthesis of saturated fatty acids (3 h); post-synthetic modifications of fatty acids: extension and desaturation; uncommon fatty acids: ricinoleic, vernolic and tuberculostearic acids; eicosanoids and prostaglandins (PG); biosynthesis of PG 2 (3 h); polyketides: structure and biosynthesis; polyketide synthase (type I, II and III PKS), biosynthesis of antibiotic macrolides (erythromycin A), structure of the 6-DEBS enzyme (3 h); biosynthesis of aromatic polyketides: orsellinic acid and phloracetophenone, biosynthesis of cannabinoids (3 h)
The mevalonate pathway: terpenoids and steroids; biosynthesis of mevalonic acid, DMAPP and IPP, classification of linear terpenoids; biosynthesis of monoterpenes: GPP, LPP and NPP; menthyl cation and biosynthesis of several cyclic monoterpens (3 h); biosynthesis of sesquiterpenes; antimalarial sesquiterpenes (artemisinin derivatives), biosynthesis of diterpenes, anticancer diterpenes (toxoids), biosynthesis of triterpenes: squalene and lanosterol (3 h); steroids and sterols: structure, stereochemistry and nomenclature, biosynthesis of cholesterol, primary and secondary bile acids, biosynthesis of cholic acid (3 h)
The shikimate pathway: biosynthesis of shikimic acid, tannins, catechins, biosynthesis of chorismic, isochorismic and prephenic acid; chorismic acid derivatives: PABA and L-tryptophan (3 h); biosynthesis of aromatic amino acids and L-DOPA, biosynthesis of phenylpropanoids: lignans and lignins, salicylic acid and salicin; biosynthesis of coumarins: dicoumarol and warfarin; biosynthesis of aromatic polyketides: flavonoids and stilbenes (3 h)
Alkaloids: generalities and classification; biosynthesis of ornithine, nicotine, piperine, tropines: hyoscyamine, atropine, cocaine; indolic alcaloids: serotonin and melatonin (3 h) Didactic methods
- Classes are held weekly in the classroom and the exposure takes place by means of power-point slides
Learning assessment procedures
- The aim of the exam is to verify at which level the learning objectives previously described have been acquired. The exam consists of an oral examination involving a topic to choose by the student
Reference texts
- P. M. Dewick - Chemistry, biosyntesis and bioactivity of organic natural substances - Second Edition - John Wiley & Sons Ltd, 2002
J.Mann - Chemical aspects of biosynthesis - Oxford science publications – 1994.
