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.

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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.
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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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64 References

Data provided by Europe PubMed Central.


Perczel, 1996
Characterization of beta-bend ribbon spiral forming peptides using electronic and vibrational CD.
Yoder G, Keiderling TA, Formaggio F, Crisma M, Toniolo C., Biopolymers 35(1), 1995
PMID: 7696550

Toniolo, J. Am. Chem. Soc. 118(), 1996
Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins.
Krimm S, Bandekar J., Adv. Protein Chem. 38(), 1986
PMID: 3541539

Dwivedi, Biopolymers 23(), 1984

Keiderling, 2000

Yoder, J. Am. Chem. Soc. 119(), 1997
Structure refinement of cyclosporin A in chloroform by using RDCs measured in a stretched PDMS-gel.
Klages J, Neubauer C, Coles M, Kessler H, Luy B., Chembiochem 6(9), 2005
PMID: 16138307

Kummerlöwe, TrAC Trends Anal. Chem. 28(), 2009

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