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The course deals with advanced parts of organic chemistry. Aim of this course is to inform, update, and encourage students about the newest topics and trends in organocatalysis, enzymatic synthesis, bioconjugations, and chemical biology tools. Basics, as well as the most recent topics from each field, will be discussed, based on the recent publications in top chemistry journals.
The list of topics for 2024/2025 semester (1) Catalysis via enamines as intermediates: Aldol reaction, Mannich reaction, alpha funcionalization of carbonyl compounds with heteroatoms, Michael addition. – (Pavel Kočovský) (2) Catalysis via iminium ions as intermediates: Cycloadditions, Michael addition (addition to enones, epoxidation, Friedel-Crafts reaction, transfer hydrogenation, multicomponent "domino" reactions). – (Pavel Kočovský) (3) Catalytic reactions controlled by hydrogen bonding: Michael addition, Mannich reaction, aza-Henry reaction, Robinson annulation, hydrocyanation, Morita-Baylis-Hillman reaction, Pictet-Spengler reaction, Diels-Alder reaction. – (Pavel Kočovský) (4) Reactions catalyzed by Brønsted acids: aldol reaction, aza-Friedel-Crafts reaction, transfer hydrogenation, Morita-Baylis-Hillman reaction. – (Pavel Kočovský) (5) Reactions catalyzed by Lewis bases: Nucleophilic allylation of aldehydes, aldol-type reactions, hydrocyanation, hydrosilylation, reductive amination. – (Pavel Kočovský) (6) Biocatalysis – (Eliška Matoušová) Features of biocatalysis, biocatalytic reactions, and their use in organic synthesis. (7) Chemical Linkers – (Ondřej Baszczyňski) This lecture will focus on chemistry of linkers as tools in chemical biology and biology. We will go through structure and function of permanent and self-immolative linkers. (8) Bioconjugations I – (Ondřej Baszczyňski) The lecture will cover the development of click-chemistry and its application to bio-conjugations. Then, we examine the covalent modification of proteins. Reactivity, chemo-selectivity, scope of particular reactions, and practical aspects will also be discussed. (9) Bioconjugations II – (Milan Vrábel) This lecture will broaden knowledge in bioconjugations including click-chemistry and Inversed Electron Diels Alder reactions. In vivo click reactions will also be discussed. (10) Chemical probes for chemical biology – (Jiří Míšek) The lecture will address the development and applications of various chemical approaches in chemical biology, including activity-based protein profiling, fluorescent probes, arrays, DNA-encoded libraries, etc. also, the impact of the field on developments in modern biomedical research will be discussed. (11) Chemical Biology methods – (Jiří Míšek) Directed enzyme evolution, site-directed mutagenesis, CRISPR/Cas9, metagenomics. For Ph.D. and ERASMUS students in English. Last update: Baszczyňski Ondřej, Ing., Ph.D. (27.09.2024)
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Jedná se o přehledné články vycházející zejména v časopisech: Nature, Science, Chemical Reviews, Chemical Society Reviews, Angewandle Chemie International Edition, European Journal of Organic Chemistry. Speciální elektronické materiály nejsou k dispozici. Recomended literature mostly consist of review articles from top journals such as: Nature, Science, Chemical Reviews, Chemical Society Reviews, Angewandle Chemie International Edition, European Journal of Organic Chemistry. Special electronic materials are not included. Last update: Baszczyňski Ondřej, Ing., Ph.D. (27.09.2024)
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Písemná a ústní zkouška v rozsahu přednášené látky a dodaných aktuálních materiálů z časopisecké literatury. Written and oral exam.
Informace o způsobu výuky v případě zavedení distančního studia. Information regarding remore (online) teaching. a) Přednášky budou probíhat přes internet (zřejmě přes Google Meet). Lectures will be presneted online. b) Adresa konání přednášky bude zaslána přes SIS před zahájením. The address of a presentation will be sent to you priot to the respective presentation. c) Ke komunikaci se mají (musí) používat pouze adresy s příponou: @natur.cuni.cz. V případě používaní jiných adres nelze zaručit správnou kvalitu spojení a přístup. Upozornění: Tyto informace se mohou měnit na základě bezprostředních změn v závislosti na změně vnitřních doporučení a předpisů odrážejících epidemiologickoou situaci. If there will be any changes, you will be informed in due time.
Last update: Baszczyňski Ondřej, Ing., Ph.D. (27.09.2024)
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Syllabus: Seminar on Advanced Organic Chemistry - 2024/25
The list of topics for 2024/2025 semester (1) Catalysis via enamines as intermediates: Aldol reaction, Mannich reaction, alpha funcionalization of carbonyl compounds with heteroatoms, Michael addition. – (Pavel Kočovský) (2) Catalysis via iminium ions as intermediates: Cycloadditions, Michael addition (addition to enones, epoxidation, Friedel-Crafts reaction, transfer hydrogenation, multicomponent "domino" reactions). – (Pavel Kočovský) (3) Catalytic reactions controlled by hydrogen bonding: Michael addition, Mannich reaction, aza-Henry reaction, Robinson annulation, hydrocyanation, Morita-Baylis-Hillman reaction, Pictet-Spengler reaction, Diels-Alder reaction. – (Pavel Kočovský) (4) Reactions catalyzed by Brønsted acids: aldol reaction, aza-Friedel-Crafts reaction, transfer hydrogenation, Morita-Baylis-Hillman reaction. – (Pavel Kočovský) (5) Reactions catalyzed by Lewis bases: Nucleophilic allylation of aldehydes, aldol-type reactions, hydrocyanation, hydrosilylation, reductive amination. – (Pavel Kočovský) (6) Biocatalysis – (Eliška Matoušová) (7) Chemical Linkers – (Ondřej Baszczyňski) (8) Bioconjugations I – (Ondřej Baszczyňski) (9) Bioconjugations II – (Milan Vrábel) (10) Chemical probes for chemical biology – (Jiří Míšek) (11) Chemical Biology methods – (Jiří Míšek)
Last update: Baszczyňski Ondřej, Ing., Ph.D. (27.09.2024)
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Learning Objectives
At the end of this course you will be able to:
(1) Understand the principles and philosophy of catalysis in general. (2) Apply various catalytic reactions for the synthesis of chiral molecules. (3) Design new catalytic cycles. (4) Design new domino processes by combining multiple reactions in one-pot without isolation of intermediates. (5) Critically assess and evaluate various potential routes to a given target molecule. (6) Assess the advantages and disadvantages of various catalytic and stoichiometric methodologies in terms of efficiency, cost, and environmental impact. (6) Design new organocatalysts. (7) Design and perform organic reaction using enzymes (8) Apply strategies for protein conjugation (9) Apply advanced strategies for click chemistry a bioconjugation (10) Apply modern chemical biology strategies in the design of your research Last update: Baszczyňski Ondřej, Ing., Ph.D. (27.09.2024)
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