Synthesis and conformational analysis of efrapeptins

Weigelt S, Huber T, Hofmann F, Jost M, Ritzefeld M, Luy B, Freudenberger C, Majer Z, Vass E, Greie J-C, Panella L, et al. (2012)
Chem. Eur. J. 18(2): 478-487.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidumare inhibitors of F(1)-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in C(α)-dialkyl amino acids (Aib, Iva, Acc) and contain one β-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogues of efrapeptin C were synthesized using α-azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F(1)-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 3(10)-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 3(10)-helical conformation.
Stichworte
Protein Structure; Secondary; Peptides/pharmacology; Peptides/chemistry; Peptides/chemical synthesis; Biomolecular; Nuclear Magnetic Resonance; Amino Acid Sequence; Adenosine Triphosphatases/antagonists & inhibitors; Anti-Bacterial Agents/chemistry; Anti-Bacterial Agents/chemical synthesis; Anti-Bacterial Agents/pharmacology; Circular Dichroism; Escherichia coli/enzymology; Hypocreales/chemistry; Models; Molecular Sequence Data; Molecular
Erscheinungsjahr
2012
Zeitschriftentitel
Chem. Eur. J.
Band
18
Ausgabe
2
Seite(n)
478-487
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/2499381

Zitieren

Weigelt S, Huber T, Hofmann F, et al. Synthesis and conformational analysis of efrapeptins. Chem. Eur. J. 2012;18(2):478-487.
Weigelt, S., Huber, T., Hofmann, F., Jost, M., Ritzefeld, M., Luy, B., Freudenberger, C., et al. (2012). Synthesis and conformational analysis of efrapeptins. Chem. Eur. J., 18(2), 478-487. doi:10.1002/chem.201102134
Weigelt, S., Huber, T., Hofmann, F., Jost, M., Ritzefeld, M., Luy, B., Freudenberger, C., Majer, Z., Vass, E., Greie, J. - C., et al. (2012). Synthesis and conformational analysis of efrapeptins. Chem. Eur. J. 18, 478-487.
Weigelt, S., et al., 2012. Synthesis and conformational analysis of efrapeptins. Chem. Eur. J., 18(2), p 478-487.
S. Weigelt, et al., “Synthesis and conformational analysis of efrapeptins”, Chem. Eur. J., vol. 18, 2012, pp. 478-487.
Weigelt, S., Huber, T., Hofmann, F., Jost, M., Ritzefeld, M., Luy, B., Freudenberger, C., Majer, Z., Vass, E., Greie, J.-C., Panella, L., Kaptein, B., Broxterman, Q.B., Kessler, H., Altendorf, K., Hollósi, M., Sewald, N.: Synthesis and conformational analysis of efrapeptins. Chem. Eur. J. 18, 478-487 (2012).
Weigelt, Sven, Huber, Thomas, Hofmann, Frank, Jost, Micha, Ritzefeld, Markus, Luy, Burkhard, Freudenberger, Christoph, Majer, Zsuzsanna, Vass, Elemér, Greie, Jörg-Christian, Panella, Lavinia, Kaptein, Bernard, Broxterman, Quirinus B, Kessler, Horst, Altendorf, Karlheinz, Hollósi, Miklós, and Sewald, Norbert. “Synthesis and conformational analysis of efrapeptins”. Chem. Eur. J. 18.2 (2012): 478-487.

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