Bioorganic Chemistry

Lectures

Lecture

Organische Chemie

Kurt Faber, Joerg Schrittwieser

VO, 2.5 st. (SS), 3 st. (WS)

Content: Part I (SS, Kurt Faber)

  • Structure & bonding of organic molecules
  • Alkanes
  • Reactions of alkanes: pyrolysis, radical halogenation
  • Cyclic alkanes, stereoisomerism
  • Reactions of alkyl halides: nucleophilic substitution, elimination
  • Alcohols
  • Reactions of alcohols
  • Ethers
  • Alkenes
  • Reactions of alkenes
  • Alkynes
  • Reactions of alkynes
  • Delokalized π-systems

Content: Part II (WS, Joerg Schrittwieser)

  • Review: Aromatic hydrocarbons—Criteria of aromaticity
  • Reactions of arenes
  • Properties and reactions of selected substituted arenes
  • Heteroarenes—Properties, categorisation, selected heterocyclic syntheses
  • Carbonyl compounds: Aldehydes and ketones
  • Nucleophilic addition reactions to carbonyl compounds
  • Reactions at the carbonyl-Cα: Enols and enolates
  • α,β-Unsaturated carbonyl compounds—Properties and reactions
  • ‘Umpolung’ of carbonyl activity
  • Carboxylic acids and their derivatives
  • Amines—Properties and reactions
  • Amine derivatives: Imines, enamines, oximes, hydrazones
  • Nitroalkanes and nitroalkenes
  • Rearrangement reactions
  • Organometallic compounds and transition metal catalysis

Recommended Textbooks:

  • J. Clayden, N. Greeves, S. Warren: Organic Chemistry, 2nd ed., Oxford University Press, 2012.
  • K. P. C. Vollhardt, N. E. Schore: Organische Chemie, 5. Auflage, Wiley-VCH, 2011.
  • P. Y. Bruice: Organische Chemie, 5. Auflage, Pearson, 2007.
  • T. Okuyama, H. Maskill: Organic Chemistry: A mechanistic approach, Oxford University Press, 2013.
  • D. Klein: Organic Chemistry, 2nd ed., Wiley, 2014.

Lecture

Organic Chemistry II

Wolfgang Kroutil, Rolf Breinbauer

VO, 2.66 st. (SS)

Content:

Modern organic chemistry will be taught, like the use of metal catalysis (for oxidation & reduction reactions, C-C and C=C bond formation and rearrangements), selective reductions and oxidations, rearrangements, cascade reactions and the usage of ionic liquids. The knowledge about heteroaromatic compounds will be widened. Furthermore protecting group strategies, the production and mechanisms of indicators/organic pigments and the synthesis of petides, DNA and bioactive compounds will be discussed. In a separate chapter the basics for ‘green’ chemistry will be discussed.

  • Basics
  • Synthetic methods
  • Carbon-carbon bond formation
    Reduction
    Oxidation
    Substitution
    Elucidation of reaction mechanisms
  • Synthetic techniques
  • Planning of syntheses
    Protective groups
    Synthesis of biopolymers
  • Green chemistry

Recommended Textbooks:

  • P. Y. Bruice, Organic Chemistry 4th ed., Pearson Education, Inc., 2004, ISBN 0-13-121730-5.
  • J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, 2000, ISBN 0-19-850346-6.
  • E. Breitmaier, G. Jung, Organische Chemie II, G. Thieme Verlag, Stuttgart-New York, 1983, ISBN 3-13-541601-1.
  • J. March, Advanced Organic Chemistry, Wiley, 1992, ISBN 0-471-60180-2.

Lecture

Asymmetrische Synthese

Wolfgang Kroutil

VO, 2 st. (WS)

Content:

After a repetition of the basics of stereochemistry, different methods of synthesising chiral molecules will be discussed. Five principles of asymmetric synthesis will show the development of the field over the past few decades. Special emphasis will be laid on methods that use a chiral reagent or chiral catalyst, e.g., chiral borohydrides, Sharpless epoxidation, Jacobsen epoxidation, Sharpless dihydroxylation, etc. In addition to the organocatalytic and metallocatalytic methods also biocatalytic options will be discussed.

  • Introduction: Chirality
  • Biological significance of chirality
  • Analytical methods
  • Asymmetric synthesis
  • strategies for asymmetric synthesis
    kinetic & thermodynamic considerations
    non-linear effects, asymmetric autocatalysis
    1st generation & chiral pool
    2nd generation – chiral auxiliary
    3rd generation – chiral complexation
    4th generation – chiral reagents
    5th generation – asymmetric catalysis

Recommended Textbooks:

  • R. A. Aitken, S. N. Kilenyi (eds.), Asymmetric Synthesis, Blackie, London, 1995.
  • I. Ojima (ed.), Catalytic Asymmetric Synthesis, Wiley-VCH, New York, 2000.
  • D. J. Ager (ed.), Handbook of Chiral Chemicals, Marcel Dekker, New York, 1999.

Lecture

Biokatalyse

Kurt Faber

VO, 2 st. (SS)

Content:

  • Application of natural catalysts—enzymes and/or whole microbial cells—to the synthesis of organic compounds
  • Properties of enzymes, pro's and con's of biocatalysts in comparison to chemical catalysts
  • Selectivities: Chemo-, regio-, diastereo- and enantio-selectivity
  • Biological properties of enantiomers, pro's and con's of isolated enzymes versus whole cells
  • Enzyme mechanisms, coenzymes, enzyme sources
  • hydrolysis
    reduction
    oxidation
    formation of C–C bonds
    addition and elimination-reactions
    halogenation and dehalogenation
    glycoside-synthesis
    rearrangement reactions
  • Special techniques: catalytic antibodies, membrane reactors, immobilization
  • Status quo and future developments

Recommended Textbook:

  • K. Faber, Biotransformations in Organic Chemistry – A Textbook, 6th rev. & corr. ed., Springer, Heidelberg, 2011

Lecture

Retrosynthesis and Planning of Organic Synthesis

Mélanie Hall

VO, 1.33 st. (SS)

Content:

Introduction into the planning of organic synthesis from easily obtainable starting materials (synthons):

  • Retrosynthetic concept by Corey
  • Reactions and interconversions of functional groups
  • Controlled synthesis
  • Protecting group techniques

Recommended Textbooks:

  • S. Warren, P. Wyatt, Organic Synthesis: The Disconnection Approach, 2nd ed., Wiley, Chichester, 2008.
  • C. L. Willis, M. Wills Syntheseplanung in der Organischen Chemie, Wiley-VCH, Weinheim, 1997.
  • T. Wirth, Syntheseplanung – aber wie?, Spektrum, Heidelberg, 1998.
  • J.-A. Gewert, J. Görlitzer, S. Götze, J. Looft, P. Menningen, T. Nöbel, H. Schirok, C. Wulff, Organic Synthesis Workbook, Wiley-VCH, Weinheim, 2000.

Seminar

DissertandInnen-Seminar in Chemie

Wolfgang Kroutil

SE, 2 st. (WS & SS)

Content:

Short oral presentations by PhD students at the Institute of Chemistry, lectures of invited guests.

Textbook

Biotransformations in Organic Chemistry – A Textbook

Biotransformations in Organic Chemistry

The use of biocatalysts, employed either as isolated enzymes or whole microbial cells, offers a remarkable arsenal of highly selective transformations for state-of-the-art synthetic organic chemistry. Over the last two decades, this methodology has become an indispensable tool for asymmetric synthesis, not only at the academic level, but also on an industrial scale.

This well-established textbook on biocatalysis provides a basis for undergraduate and graduate courses in modern organic chemistry, as well as a condensed introduction into this field. After a basic introduction into the use of biocatalysts—principles of stereo-selective transformations, enzyme properties and kinetics—the different types of reactions are explained according to the ‘reaction principle’, such as hydrolysis, reduction, oxidation, C–C bond formation, etc. Special techniques, such as the use of enzymes in organic solvents, immobilization techniques and modified or artificial enzymes, are treated in a separate section. A final chapter deals with the basic rules for the safe and practical handling of biocatalysts.

In this completely revised 6th edition, emphasis has been given to an improved didactic style including colored graphics in order to facilitate a deeper understanding of the underlying principles. New developments, such as transamination, enzyme promiscuity and applications on industrial scale within the field of ‘white biotechnology’ are included.

Further information: springer.com