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
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Jost, Micha;
Weigelt, Sven;
Huber, Thomas;
Majer, Zsuzsanna;
Greie, Joerg-Christian;
Altendorf, Karlheinz;
Sewald, NorbertUniBi 
Einrichtung
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.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
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
Hu Q, Li F, Zhang Y., Biomed Res Int 2016(), 2016
PMID: 27144161
Synthesis and conformational properties of a TOAC doubly spin-labeled analog of the medium-length, membrane active peptaibiotic ampullosporin A as revealed by CD, fluorescence, and EPR spectroscopies.
Milov AD, Tsvetkov YD, Bortolus M, Maniero AL, Gobbo M, Toniolo C, Formaggio F., Biopolymers 102(1), 2014
PMID: 23896794
Milov AD, Tsvetkov YD, Bortolus M, Maniero AL, Gobbo M, Toniolo C, Formaggio F., Biopolymers 102(1), 2014
PMID: 23896794
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
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
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
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
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
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
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
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.
Morphological alterations accompanying the effect of peptaibiotics, alpha-aminoisobutyric acid-rich secondary metabolites of filamentous fungi, on Culex pipiens larvae.
Matha V, Jegorov A, Kiess M, Bruckner H., Tissue Cell 24(4), 1992
PMID: 1359675
Matha V, Jegorov A, Kiess M, Bruckner H., Tissue Cell 24(4), 1992
PMID: 1359675
Structure determination of neoefrapeptins A to N: peptides with insecticidal activity produced by the fungus Geotrichum candidum.
Fredenhagen A, Molleyres LP, Bohlendorf B, Laue G., J. Antibiot. 59(5), 2006
PMID: 16883776
Fredenhagen A, Molleyres LP, Bohlendorf B, Laue G., J. Antibiot. 59(5), 2006
PMID: 16883776
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
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
MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures.
Kraulis PJ., J Appl Crystallogr 24(5), 1991
PMID: c6694
Kraulis PJ., J Appl Crystallogr 24(5), 1991
PMID: c6694
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
Nagaraj G, Uma MV, Shivayogi MS, Balaram H., Antimicrob. Agents Chemother. 45(1), 2001
PMID: 11120957
Jost, Angew. Chem., Int. Ed. 41(), 2002
Spermidine as a potential biosynthetic precursor to the 1,5-diazabicyclo[4:3:o]nonene residue in the efrapeptins.
Uma MV, Sudha R, Balaram P., J. Pept. Res. 58(5), 2001
PMID: 11892846
Uma MV, Sudha R, Balaram P., J. Pept. Res. 58(5), 2001
PMID: 11892846
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
Abrahams JP, Leslie AG, Lutter R, Walker JE., Nature 370(6491), 1994
PMID: 8065448
The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.
Seebach D, Beck AK, Bierbaum DJ., Chem. Biodivers. 1(8), 2004
PMID: 17191902
Seebach D, Beck AK, Bierbaum DJ., Chem. Biodivers. 1(8), 2004
PMID: 17191902
beta-Peptides: from structure to function.
Cheng RP, Gellman SH, DeGrado WF., Chem. Rev. 101(10), 2001
PMID: 11710070
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
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
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
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
Structural characteristics of alpha-helical peptide molecules containing Aib residues.
Karle IL, Balaram P., Biochemistry 29(29), 1990
PMID: 2204420
Karle IL, Balaram P., Biochemistry 29(29), 1990
PMID: 2204420
Karle, Proteins Struct. Funct. Genet. 7(), 1990
Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide units.
Venkatachalam CM., Biopolymers 6(10), 1968
PMID: 5685102
Venkatachalam CM., Biopolymers 6(10), 1968
PMID: 5685102
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 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
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
HOLZWARTH G, DOTY P., J. Am. Chem. Soc. 87(), 1965
PMID: 14228459
Theoretical CD studies of polypeptide helices: examination of important electronic and geometric factors.
Manning MC, Woody RW., Biopolymers 31(5), 1991
PMID: 1868170
Manning MC, Woody RW., Biopolymers 31(5), 1991
PMID: 1868170
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
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
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
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
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
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
Steffens K, Schneider E, Deckers-Hebestreit G, Altendorf K., J. Biol. Chem. 262(12), 1987
PMID: 2883181
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 17589859
PubMed | Europe PMC
Suchen in
Google Scholar