6 ECTS credits
150 h study time
Offer 1 with catalog number 4018294ENR for all students in the 1st and 2nd semester at a (E) Master - advanced level.
In this course, the occurence, properties and chemical synthesis of some important classes of natural products are discussed. The course is composed of two main parts, i.e. a part dealing with peptide chemistry (Prof. D. Tourwé and Prof. S. Ballet) and a part dealing with non-peptide natural products (Prof. G. Verniest). The content of the first part is identical as the content of the course ‘Synthesis and Structure of Peptides’ (D. Tourwé) and is taught in the first semester. The second part consists of a part of the course ‘Natural Product Chemistry’ (G. Verniest) which is taught in the second semester.
In the first part and after an introductory chapter on peptide chemistry, the following topics are discussed:
1. Peptide synthesis (Protection schemes, coupling procedures, solution synthesis, solid phase synthesis)
2. Peptide conformations (Flexibility, secondary structure elements, conformational analysis by NMR, pseudopeptides and mimetics)
3. Limitations of natural peptides (Conformational constraints, replacements of the peptide bond, metabolic stabilization, enzyme inhibitors, synthetic methods).
In the second main part, dealing with non-peptidic natural products, the focus is directed to the organic synthesis of natural products with special attention to the various reaction mechanisms. Also in this part, the described natural products are discussed in terms of their properties, relevance, use and in some cases their industrial preparation. The overview given below is not a comprehensive list of all possible natural products, but gives the student an idea of some important classes of compounds that affect our daily life (e.g. antibiotics, toxins, agrochemicals, etc.)
During the practical laboratory exercises (WPO), a few synthetic projects will be given to each student. These may vary from year to year, depending on the scientific research going on that moment. The syntheses are always related to the synthesis of a natural product, a precursor or a natural product analogue. The students will become acquainted with general and advanced principles of the chemical synthesis, purification techniques and analysis (recording NMR-spectra and FT-IR spectra).
The aim of the independant work by the student is to analyze a flow diagram of an industrial process of a biooragnic compound. This follows the lecture of 'reaction upscaling'.
Course notes of 'Synthesis and Structure of Peptides' as well as 'Natural Product Chemistry' (available at VUBtiek) can be used.
Copies of powerpoint slides or transparancies will be provided (hard copy and/or on-line pdf).
Additional study material:
The student
*knows how to design and synthesize a peptide.
*possesses insights on the conformation adopted by small peptides.
*possesses knowledge of recent research developments in the peptide field.
*has a notion of the most important classes of natural products and is able to situate those compounds in terms of bioactivity, properties and chemical structure. The student can recognize chemical structures as natural products or related compounds and situate these in their context.
*can understand in detail the synthetic pathways to prepare natural products (in industry or at laboratory scale) and is able to explain reaction mechanisms of modern organic synthesis (without learning synthetic schemes by haert).
*has notion of some basic principles in reaction upscaling in the industrial synthesis of organic compounds.
*can apply the different synthetic strategies to design pathways to prepare related but different organic structures.
*can execute and analyse organic reactions in the laboratory using modern methods.
*can consult scientific literature regarding organic chemistry via focussed search actions in databases.
*can report (written) and communicate on topics in bioorganic chemistry in a scientific manner and develops a sense for detail and critical analysis of obtained or published data in (bio)organic chemistry.
The final grade is composed based on the following categories:
Oral Exam determines 70% of the final mark.
PRAC Practical Assignment determines 20% of the final mark.
SELF Practical Assignment determines 10% of the final mark.
Within the Oral Exam category, the following assignments need to be completed:
Within the PRAC Practical Assignment category, the following assignments need to be completed:
Within the SELF Practical Assignment category, the following assignments need to be completed:
The students needs to pass both partims. When the student does not pass for one partim, the final total score is equal to the score of the partim with the lowest score. Upon re-examination (e.g. in Aug/Sept), the student does not need to retake the exam for the partim which (s)he passed in previous exam periods.
The practical exercises (WPO) are mandatory (100% presence during the WPO). In case of legal absence, the laboratory exercises can be re-scheduled upon approval of the principal instructor, at the latest before the start of the examination period of the second semester. The student notifies the principal instructor in such case as soon as possible to schedule a date for these exercises. For the evaluation of the practicals, the following categories and attitudes are quoted: reports, answer to questions during the exercises, preparation, performance in the laboratory, including correct experimental setup, cleanliness and organisation. Students who are illegitimately absent cannot retake the practical exercises and are quoted pro rata the amount of missed exercises. Students who were illegitimately absent on two practical sessions are excluded from the exam.
The oral exam is divided in two parts (different moments), part 1: peptide chemistry, part 2: natural product chemistry.
Part 1: during the exam, the student needs to present and discuss an in advanced prepared paper on peptide synthesis; propose a strategy for a virtual peptide synthesis and discuss the used methods; comment on a conformational problem
Part 2: oral exam on natural product chemistry with written preparation (oral exam ca. one hour per person, written preparation is also quoted and used in the final grading)
This offer is part of the following study plans:
Master of Bioengineering Sciences: Chemistry and Bioprocess Technology: Chemical Biotechnology (only offered in Dutch)
Master of Bioengineering Sciences: Chemistry and Bioprocess Technology: Biochemical Biotechnology (only offered in Dutch)