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Elements of natural products chemistry

Program: 
Chemistry
ECTS: 
5
Lecturer: 
Dr hab. Piotr Stefanowicz (piotr.stefanowicz @chem.uni.wroc.pl), Dr Marek Cebrat (marek.cebrat@chem.uni.wroc.pl)
Type: 
Optional
Lecture
Number of hours: 
1h X 15 weeks = 15 hours (1 semester)
Laboratory
Number of hours: 
2h X 15 weeks = 30 hours (1 semester)
Objective: 

To understand the classification and biosynthesis of natural products.
To select appropriate methods of natural products investigation depending on their structures and physicochemical properties.
To develop the techniques of laboratory work including isolation purification and characterization of natural products.

Assessment: 

lecture: A writing exam
laboratory: The day-by-day assessment conducted by the instructor during the laboratory work and evaluation of written report on performed experiments

Prerequisites: 

Fully validated Fundamental Chemistry

Contents: 

Lecture (one semester 30h in total):

Primary and secondary metabolism; definition of natural product; mechanisms of selected metabolic reactions; methods of investigation the biosynthetic pathways of natural products; the examples of natural products formed from: active acetate, shikimic acid, mevalonic acid and amino acids; searching for the new, biologically active compounds, isolation purification and structure elucidation of natural products, basics of metabolomics; biological activity of natural products

Laboratory I (1 Semester, 30h,)

The isolation and purification of five natural products selected from the list: caffeine, eugenol, acetyleugenol trimiristin, theobromine, cinnamic aldehyde, cholesterol, nicotine, carotenoids, taxines); characterization of isolated compounds and assessing their purity by determination melting point, boiling point, refraction coefficient and using chromatographic methods. For three selected compounds, the purity will be additionally verified on the basis spectroscopic methods (NMR, EI-MS, ESI-MS, IR); writing reports including isolation, purification, analytical data, interpretation of spectra, biosynthetic origin and data on biological activity.

Knowledge:

  • Knows and understands the biosynthetic origin and classification of natural products

  • Understands the correlations between chemical structures of natural products and mechanisms of their biological activity

  • Is familiar with methods of isolation purification and analysis of natural products

Skills:

  • Is able to classify the natural product according to its biosynthetic origin

  • Is able to identify the natural products and to assess their purity basing on the spectroscopic and chromatographic methods.

  • Isolates and purifies chemical compounds of natural origin

  • Writes research reports

  • Assesses results of an experiment and verifies them with a literature data.

Personal and Social Competence

  • a responsibility for accurate experimental work and critical data interpretation

  • respecting laboratory safety rules