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.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Jost, Micha; Weigelt, Sven; Huber, Thomas; Majer, Zsuzsanna; Greie, Joerg-Christian; Altendorf, Karlheinz; Sewald, NorbertUniBi
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
2007
Zeitschriftentitel
Chemistry & Biodiversity
Band
4
Ausgabe
6
Seite(n)
1170-1182
ISSN
1612-1872
eISSN
1612-1880
Page URI
https://pub.uni-bielefeld.de/record/1593309

Zitieren

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. https://doi.org/10.1002/cbdv.200790103
Jost, Micha, Weigelt, Sven, Huber, Thomas, Majer, Zsuzsanna, Greie, Joerg-Christian, Altendorf, Karlheinz, and Sewald, Norbert. 2007. “Synthesis, and structural and biological studies of efrapeptin C analogues”. Chemistry & Biodiversity 4 (6): 1170-1182.
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.

9 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Risks of Mycotoxins from Mycoinsecticides to Humans.
Hu Q, Li F, Zhang Y., Biomed Res Int 2016(), 2016
PMID: 27144161
Solution synthesis, conformational analysis, and antimicrobial activity of three alamethicin F50/5 analogs bearing a trifluoroacetyl label.
De Zotti M, Ballano G, Jost M, Salnikov ES, Bechinger B, Oancea S, Crisma M, Toniolo C, Formaggio F., Chem Biodivers 11(8), 2014
PMID: 25146762
Conformational properties of secondary amino acids: replacement of pipecolic acid by N-methyl-l-alanine in efrapeptin C.
Dutt Konar A, Vass E, Hollósi M, Majer Z, Grüber G, Frese K, Sewald N., Chem Biodivers 10(5), 2013
PMID: 23681735
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 JC, Panella L, Kaptein B, Broxterman QB, Kessler H, Altendorf K, Hollósi M, Sewald N., Chemistry 18(2), 2012
PMID: 22147615
Synthesis, preferred conformation, protease stability, and membrane activity of heptaibin, a medium-length peptaibiotic.
De Zotti M, Biondi B, Peggion C, Park Y, Hahm KS, Formaggio F, Toniolo C., J Pept Sci 17(8), 2011
PMID: 21495119
The effect of NBD-Cl in nucleotide-binding of the major subunit alpha and B of the motor proteins F1FO ATP synthase and A1AO ATP synthase.
Hunke C, Tadwal VS, Manimekalai MS, Roessle M, Grüber G., J Bioenerg Biomembr 42(1), 2010
PMID: 20082212
Aib and iva in the biosphere: neither rare nor necessarily extraterrestrial.
Brückner H, Becker D, Gams W, Degenkolb T., Chem Biodivers 6(1), 2009
PMID: 19180454
Spectroscopic and crystallographic studies of the mutant R416W give insight into the nucleotide binding traits of subunit B of the A1Ao ATP synthase.
Kumar A, Manimekalai MS, Balakrishna AM, Hunke C, Weigelt S, Sewald N, Grüber G., Proteins 75(4), 2009
PMID: 19003877

44 References

Daten bereitgestellt von Europe PubMed Central.


Gupta, J. Am. Chem. Soc. 113(), 1991

Gupta, J. Org. Chem. 57(), 1992
The structure of bovine F1-ATPase complexed with the peptide antibiotic efrapeptin.
Abrahams JP, Buchanan SK, Van Raaij MJ, Fearnley IM, Leslie AG, Walker JE., Proc. Natl. Acad. Sci. U.S.A. 93(18), 1996
PMID: 8790345

AUTHOR UNKNOWN, 0
Antimalarial activities of peptide antibiotics isolated from fungi.
Nagaraj G, Uma MV, Shivayogi MS, Balaram H., Antimicrob. Agents Chemother. 45(1), 2001
PMID: 11120957

Jost, Angew. Chem., Int. Ed. 41(), 2002
Structure at 2.8 A resolution of F1-ATPase from bovine heart mitochondria.
Abrahams JP, Leslie AG, Lutter R, Walker JE., Nature 370(6491), 1994
PMID: 8065448
beta-Peptides: from structure to function.
Cheng RP, Gellman SH, DeGrado WF., Chem. Rev. 101(10), 2001
PMID: 11710070

Seebach, Helv. Chim. Acta 79(), 1996

Schumann, J. Am. Chem. Soc. 122(), 2000
Integrin alpha5beta1 ligands: biological evaluation and conformational analysis.
Zimmermann D, Guthohrlein EW, Malesevic M, Sewald K, Wobbe L, Heggemann C, Sewald N., Chembiochem 6(2), 2005
PMID: 15645521

Malešević, Int. J. Pept. Res. Ther. 12(), 2006
Effect of lengthening of peptide backbone by insertion of chiral beta-homo amino acid residues: conformational behavior of linear peptides containing alternating L-leucine and beta-homo L-leucine residues.
Rossi F, Bucci E, Isernia C, Saviano M, Iacovino R, Romanelli A, Di Lello P, Grimaldi M, Montesarchio D, De Napoli L, Piccialli G, Benedetti E., Biopolymers 53(2), 2000
PMID: 10679618
Crystal-state conformation of Calpha,alpha-dialkylated peptides containing chiral beta-homo-residues.
Romanelli A, Garella I, Menchise V, Iacovino R, Saviano M, Montesarchio D, Didierjean C, Di Lello P, Rossi F, Benedetti E., J. Pept. Sci. 7(1), 2001
PMID: 11245201

Toniolo, Macromolecules 24(), 1991

Yoder, J. Am. Chem. Soc. 119(), 1997

Karle, Proteins Struct. Funct. Genet. 7(), 1990

Toniolo, Trends Biochem. Sci. (), 1991
Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution).
Toniolo C, Crisma M, Formaggio F, Peggion C., Biopolymers 60(6), 2001
PMID: 12209474

Toniolo, J. Am. Chem. Soc. 118(), 1996

Formaggio, Chem.–Eur. J. 6(), 2000
Sensitive criteria for the critical size for helix formation in oligopeptides.
Goodman M, Verdini AS, Toniolo C, Phillips WD, Bovey FA., Proc. Natl. Acad. Sci. U.S.A. 64(2), 1969
PMID: 5261026
THE ULTRAVIOLET CIRCULAR DICHROISM OF POLYPEPTIDES.
HOLZWARTH G, DOTY P., J. Am. Chem. Soc. 87(), 1965
PMID: 14228459

Meldal, Tetrahedron Lett. 38(), 1997
Solid-phase synthesis of chemotactic peptides using alpha-azido acids.
Tornoe CW, Sengelov H, Meldal M., J. Pept. Sci. 6(7), 2000
PMID: 10946996

Bartra, Tetrahedron Lett. 28(), 1987

Bartra, Tetrahedron 46(), 1990

Müller, Synthesis (), 1998

Perczel, 0
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

Blasio, J. Am. Chem. Soc. 114(), 1992

Tichy, Collect. Czech. Chem. Commun. 49(), 1984
Properties of F1-ATPase from the uncD412 mutant of Escherichia coli.
Wise JG, Duncan TM, Latchney LR, Cox DN, Senior AE., Biochem. J. 215(2), 1983
PMID: 6228224
An automated continuous assay of membrane-bound and solube ATPases and related enzymes.
Arnold A, Wolf HU, Ackermann BP, Bader H., Anal. Biochem. 71(1), 1976
PMID: 179440
Chemical modification of the F0 part of the ATP synthase (F1F0) from Escherichia coli. Effects on proton conduction and F1 binding.
Steffens K, Schneider E, Herkenhoff B, Schmid R, Altendorf K., Eur. J. Biochem. 138(3), 1984
PMID: 6319139
Fo portion of Escherichia coli ATP synthase. Further resolution of trypsin-generated fragments from subunit b.
Steffens K, Schneider E, Deckers-Hebestreit G, Altendorf K., J. Biol. Chem. 262(12), 1987
PMID: 2883181
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