Lipase-Catalysed Preparation of Chiral Compounds

Code:

53303

ECTS:

3.0

Lecturers in charge:

prof. dr. sc. Senka Djaković

Lecturers:

prof. dr. sc. Senka Djaković - Seminar

izv. prof. dr. sc. Jasmina Lapić - Laboratory exercises

Take exam:

Studomat

Load:

1. komponenta

Lecture type	Total
Lectures	15
Seminar	4
Laboratory exercises	20

* Load is given in academic hour (1 academic hour = 45 minutes)

Description:

Biocatalysed reactions have found very broad application for the production of chiral compounds, as they are characterised by high regio- and stereoselectivity. Organic compounds are poorly soluble in aqueous media, and the discovery of enzyme activity in organic solvents opened up a new field in bioorganic chemistry. Microbial and fungal lipases are among the most readily available enzymes, which have a very broad selectivity towards substrates, but also a very high stereoselectivity. Therefore, they are used for a number of different reaction types: enantioselective synthesis of alcohols, diols, polyols and amines; synthesis of amides and peptides, transesterification of lipids, diastereoselective esterification or hydrolysis; simple acylation and deacylation under mild reaction conditions. Optically pure compounds are often used as chiral synthones in the synthesis of biologically active or industrially important compounds (pharmaceuticals, biotechnology, food industry, agriculture).

Learning outcomes:

Distinguish and list the terms of stereochemistry (stereoselectivity, stereospecificity, kinetic resolution, etc.)
Describe and analyze the enzyme / lipase selectivity of the substrate
Select and compare biotransformation reactions under different conditions
Perform stereoselective reactions, and argue and summarize the obtained results
Adapt and solve the set requirements for the synthesis of chiral compounds

Literature:

1. M. Nógrádi, Stereochemistry, Akadémiai Kiadó, Budapest, 1981.
2. L. Poppe, L Novák, Selective Biocatalysis, Wiley-VCH, Weinheim, New York, Cambridge, Basel, 1992.
3. K. Faber, Biotransformations in Organic Chemistry, Springer-VerlagBerlinHeidelbergNew York, 1997.,

Optional literature:

, 4. K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis, Wiley-VCH, Weinheim, New York, Cambridge, Tokyo, 1995.
5. U. T. Bornscheuer, R. J. Kazalauskas, Hydrolases in Organic Synthesis, Wiley-VCH, Weinheim, New York, Chichester, Brisbone, Singapore, Toronto, 1999., , , .

3. semester

Bioprocesno inženjerstvo - B1 - Regular studij - Bioprocess Engineering

Elective course - Regular studij - Bioprocess Engineering

Prehrambeno inženjerstvo - B1 - Regular studij - Food Engineering

Elective course - Regular studij - Food Engineering

Upravljanje sigurnošću hrane - B1 - Regular studij - Food Safety Management

Elective course - Regular studij - Food Safety Management

Molekularna biotehnologija - B1 - Regular studij - Molecular Biotechnology

Elective course - Regular studij - Molecular Biotechnology

Consultations schedule:

Lipase-Catalysed Preparation of Chiral Compounds