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)
Chemistry (Weinheim an der Bergstrasse, Germany) 18(2): 478-487.

Journal Article | Published | English

No fulltext has been uploaded

Author
; ; ; ; ; ; ; ; ; ; ;
All
Abstract
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.
Publishing Year
ISSN
PUB-ID

Cite this

Weigelt S, Huber T, Hofmann F, et al. Synthesis and conformational analysis of efrapeptins. Chemistry (Weinheim an der Bergstrasse, Germany). 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. Chemistry (Weinheim an der Bergstrasse, Germany), 18(2), 478-487.
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. Chemistry (Weinheim an der Bergstrasse, Germany) 18, 478-487.
Weigelt, S., et al., 2012. Synthesis and conformational analysis of efrapeptins. Chemistry (Weinheim an der Bergstrasse, Germany), 18(2), p 478-487.
S. Weigelt, et al., “Synthesis and conformational analysis of efrapeptins”, Chemistry (Weinheim an der Bergstrasse, Germany), 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. Chemistry (Weinheim an der Bergstrasse, Germany). 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”. Chemistry (Weinheim an der Bergstrasse, Germany) 18.2 (2012): 478-487.
This data publication is cited in the following publications:
This publication cites the following data publications:

3 Citations in Europe PMC

Data provided by Europe PubMed Central.

Functional expression of L-lysine α-oxidase from Scomber japonicus in Escherichia coli for one-pot synthesis of L-pipecolic acid from DL-lysine.
Tani Y, Miyake R, Yukami R, Dekishima Y, China H, Saito S, Kawabata H, Mihara H., Appl. Microbiol. Biotechnol. 99(12), 2015
PMID: 25547835
Cruentaren A binds F1F0 ATP synthase to modulate the Hsp90 protein folding machinery.
Hall JA, Kusuma BR, Brandt GE, Blagg BS., ACS Chem. Biol. 9(4), 2014
PMID: 24450340

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

Export

0 Marked Publications

Open Data PUB

Web of Science

View record in Web of Science®

Sources

PMID: 22147615
PubMed | Europe PMC

Search this title in

Google Scholar