Peptidomimetics and pseudopeptides

Course Description

Course content

Lectures

1. Biomimicry. Natural peptides and proteins. Secondary structural elements. / 2 hours

2. Disadvantages of natural peptides. Structural complementarity. / 2 hours

3. α-Helice mimetics. / 2 hour

4. Turn mimetics. / 2 hours

5. β-Sheet mimetics. / 2 hours

6. Carbohydrate and organometallic peptidomimetics. / 2 hours

7. Peptidomimetics used in biomedicine and pharmacology. / 3 hours

Laboratory practice exercises

1. Synthesis of ferrocene peptide Fca-Ala by using HOBt/ EDC method. / 5 hours

2. Isolation of prepared bioconjugates from reaction mixture. TLC-purification. / 5
hours

3. IR measurement of free and associated NH groups. / 5 hours

4. The determination of hydrogen-bonding pattern by using concentration- and
temperature-dependent NMR spectroscopy. / 5 hours

Seminars

1. Conformational analysis of ferrocene peptide by using NMR-NOESY and CD
spectroscopy. / 4 hours

Learning outcomes

On successful completion of the module, you will be able to:

1. Explain how to overcome the disadvantages of natural peptides (proteolytic
instability, polarity, conformational freedom) by using adequately designed mimetics.

2. Identify peptide and non-peptide structures that mimic the secondary structural element involved in molecular recognition.

3. Demonstrate conformational analysis of peptidomimetics by using spectroscopic
techniques (IR, NMR and CD). Evaluate the potential pharmacological and
biotechnological application of peptidomimetics

Teaching practices and methods

Lectures and laboratory practice exercices.

Evaluation of student learning

Oral report - presentation.

Literature

Literature list

1. N. T. Ross et al, Synthetic mimetics of proteine secondary structure domains, Phil.
Trans. R. Soc. A, 368, 2010, 989.

2. R. M. J. Liskamp et al, Peptides and Proteins as a Continuing Exciting Source of
Inspiration for Peptidomimetics. ChemBioChem 2011, 12, 1626.

3. E. Ko et al, Minimalist and universal peptidomimetics, Chem. Soc. Rev. 2011, 40,
4411.

4. L. Barišić et al, Synthesis and Conformational Analysis of Methyl N-Alanyl-
1'-aminoferrocene-1-carboxylate. Eur. J. Inorg. Chem. 2012, 11, 1810.

5. E. Lohof et al, Sugar Amino Acids and Carbohydrates as Scaffolds and
Peptidomimetics. JAI Press,Stanford, 2002.