Organic Chemistry of Biological Processes - MC270P99

• Anglický název: Organic Chemistry of Biological Processes
• Český název: Organická chemie biologických procesů
• Zajišťuje: Katedra organické chemie (31-270)
• Fakulta: Přírodovědecká fakulta
• Platnost: od 2024
• Semestr: letní
• E-Kredity: 3
• Způsob provedení zkoušky: letní s.:písemná
• Rozsah, examinace: letní s.:2/1, Zk [HT]
• Počet míst: neomezen
• Minimální obsazenost: 3
• 4EU+: ne
• Virtuální mobilita / počet míst pro virtuální mobilitu: ne
• Stav předmětu: vyučován
• Jazyk výuky: angličtina
• Úroveň: specializační
• Poznámka: povolen pro zápis po webu
• Garant: prof. Ing. Pavel Kočovský
• Neslučitelnost : MC270P87

Anotace

čeština

Kurs pokrývá chemické reakce probíhající v živé hmotě jako paralela k reakcím známým z laboratoře: enzymy katalyzovaná nukleofilní substituce, elektrofilní adice, Michaelova adice, eliminace, aldolová reakce, Claisenova kondenzace, aminace-deaminace, oxidace, redukce, molekulární přesmyky a kaskádové reakce. Stereochemie jednotlivých procesů, izotopové značení. Úloha vybraných biomolekul v živém organismu. Biosyntéza vybraných biomolekul a možnosti jejich ovlivnění s výhledem na vývoj nových léčiv. Mechanismus účinku vybraných léčiv na molekulární úrovni a využití těchto znalostí k vývoji nových farmak.

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (11.09.2024)

angličtina

The course will deal with chemical reactions proceeding in the living matter as a parallel to the reactions known from the organic chemistry laboratory. The following topics will be covered:
(1) Enzyme-catalyzed nucleophilic substitution, electrophilic addition, Michael addition, elimination, aldol reaction, Claisen condensations, amination-deamination, molecular rearrangements, and domino reactions, etc.
(2) Stereochemistry of the individual processes and isotopic labelling as a tool for elucidation of reaction mechanisms.
(3) The role of selected biomolecules in living organisms
(4) Biosynthesis of selected biomolecules and the methods for its artificial control with a view of development of new medicinal drugs.
(5) Mechanism of action of selected medicinal drugs and poisons (e.g., novichok) at a molecular level and the application of this knowledge for the development of new drugs.

Knowledge of standard organic chemistry and good arrow-pushing skills are a prerequisite. Passing a basic biochemistry course before attending this course is not required but would desirable.

Complete course materials will be handed out as a supplement to the lectures and tutorials.

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (07.06.2018)

Literatura

čeština

Základní literatura:

J. E. McMurry, T. Begley: The Organic Chemistry of Biological Pathways, 2nd edition, Roberts & Co Publishers, Greenwood Village, Colorado, 2016 (ISBN 9781936221561)

Doporučená literatura:

D. Van Vranken, G. A. Weiss: Introduction to Bioorganic Chemistry and Chemical Biology,  Garland Science, 2012,   (ISBN 9780815342144)

Poslední úprava: Rubešová Jana, RNDr., Ph.D. (01.04.2018)

angličtina

Basic literature:

J. E. McMurry, T. Begley: The Organic Chemistry of Biological Pathways, 2nd edition, Roberts & Co Publishers, Greenwood Village, Colorado, 2016 (ISBN 9781936221561)

Recommended literature:

D. Van Vranken, G. A. Weiss: Introduction to Bioorganic Chemistry and Chemical Biology, Garland Science, 2012,   (ISBN 9780815342144)

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (07.06.2018)

Sylabus

This course is focused on a detailed mechanistic description of fundamental reactions proceeding in living organisms as a parallel to the reactions known from chemical laboratory. The following reactions, known from the course on organic chemistry, will thus be shown in new light – as part of enzyme-catalyzed processes:

(1) Nucleophilic substitution

(2) Electrophilic additions

(3) Elimination reactions

(4) Electrophilic aromatic substitution

(5) Redox reactions

(6) Aldol reactions

(7) Claisen condensation

(8) Molecular rearrangements (e.g., Wagner-Meerwein and Claisen rearrangements)

(9) Pericyclic reactions (e.g., 6π-electron cyclization in the biosynthesis of vitamin D)

(10) Radical reactions

(11) Carbene-catalyzed reaction (e.g., those using vitamin B₁ as a coenzyme)

(12) Reactions catalyzed by iron complexes (e.g., cytochrome)

(13) Cascade transformations

(14) Photocatalytic reactions

 

The course will also focus on the following topics:

(1) Stereochemistry of individual reactions

(2) Isotopic labeling for elucidation of reaction mechanisms

(3) Fluorescent probes for elucidation of processes in living cells

(4) The role of selected biomolecules in living organisms

(5) Biosynthesis of selected biomolecules (e.g., lipids, steroids, carbohydrates, antibiotics)

(6) Mechanism of action of selected medicinal drugs at a molecular level

(7) Design of new medicinal drugs based on their interference in certain metabolic pathways

(8) Concept of prodrugs (incl. the principle of self-immolative linkers)

(9) Targeted delivery of medicinal drugs to the cell (namely click chemistry)

(10) Controlled release of drugs in the cell by specific chemical reactions

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (11.09.2024)

Vstupní požadavky

Znalost organické chemie a biochemie v rozsahu přednášek chemických bakalářských oborů.

Poslední úprava: Rubešová Jana, RNDr., Ph.D. (01.04.2018)

Výsledky učení

This course will help you understand biochemical reactions that are not detailed in lectures on biochemistry. At its end you should be able to:

(1) Propose a mechanism for an enzymatic reaction not previously seen.

(2) Suggest a method for probing that mechanism.

(3) Suggest a fluorescent probe to elucidate the events in a living cell.

(4) Figure out the mechanism of action of medicinal drugs.

(5) Design new medicinal drugs based on the known mechanism of biochemical processes.

(6) Design a target delivery system for medicinal drugs.

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (11.09.2024)