Synthesis, and structural and biological studies of efrapeptin C analogues

Jost M, Weigelt S, Huber T, Majer Z, Greie J-C, Altendorf K, Sewald N (2007)
CHEMISTRY & BIODIVERSITY 4(6): 1170-1182.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
A series of analogues of efrapeptin C (1), with variations in the central tripeptide epitope (positions 6-8), were prepared by a combination of solid- and solution-phase peptide syntheses. The conformations of the modified compounds 2-6 were investigated by circular-dichroism (CD) spectroscopy to differentiate between 3(10)- and alpha-helical secondary structures. The inhibitory activities of the new compounds towards F-1-ATPase from E. coli were determined. The modified congeners 3-5 were less active by one order of magnitude compared to 1 (K-i 10 mu m), and 6 was completely inactive. Our experiments demonstrate that the flexible, central tripeptide epitope, comprising positions 6-8 in 1, is crucial for molecular recognition, even slight sequence modifications being hardly tolerated.
Erscheinungsjahr
Zeitschriftentitel
CHEMISTRY & BIODIVERSITY
Band
4
Zeitschriftennummer
6
Seite
1170-1182
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eISSN
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Jost M, Weigelt S, Huber T, et al. Synthesis, and structural and biological studies of efrapeptin C analogues. CHEMISTRY & BIODIVERSITY. 2007;4(6):1170-1182.
Jost, M., Weigelt, S., Huber, T., Majer, Z., Greie, J. - C., Altendorf, K., & Sewald, N. (2007). Synthesis, and structural and biological studies of efrapeptin C analogues. CHEMISTRY & BIODIVERSITY, 4(6), 1170-1182. doi:10.1002/cbdv.200790103
Jost, M., Weigelt, S., Huber, T., Majer, Z., Greie, J. - C., Altendorf, K., and Sewald, N. (2007). Synthesis, and structural and biological studies of efrapeptin C analogues. CHEMISTRY & BIODIVERSITY 4, 1170-1182.
Jost, M., et al., 2007. Synthesis, and structural and biological studies of efrapeptin C analogues. CHEMISTRY & BIODIVERSITY, 4(6), p 1170-1182.
M. Jost, et al., “Synthesis, and structural and biological studies of efrapeptin C analogues”, CHEMISTRY & BIODIVERSITY, vol. 4, 2007, pp. 1170-1182.
Jost, M., Weigelt, S., Huber, T., Majer, Z., Greie, J.-C., Altendorf, K., Sewald, N.: Synthesis, and structural and biological studies of efrapeptin C analogues. CHEMISTRY & BIODIVERSITY. 4, 1170-1182 (2007).
Jost, Micha, Weigelt, Sven, Huber, Thomas, Majer, Zsuzsanna, Greie, Joerg-Christian, Altendorf, Karlheinz, and Sewald, Norbert. “Synthesis, and structural and biological studies of efrapeptin C analogues”. CHEMISTRY & BIODIVERSITY 4.6 (2007): 1170-1182.

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